We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Vacation Rentals nearby Chilmark Chocolates

State Rd, Chilmark, Martha's Vineyard, Massachusetts
Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    C$543 Average
    |||
    |||
    C$0C$1,000+
    Suitability
    More filters
    Travellers to Chilmark are booking July dates now. Secure your vacation rental today, and have the perfect trip.
    All 100 Rentals in Chilmark
    1.7 kilometres from Chilmark Chocolates
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Charming 3br Getaway in Oak Bluffs1 / 66
    (4)Very good
    2.8 kilometres from Chilmark Chocolates
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Nestled in the Woods1 / 39
    (2)Very good
    2.2 kilometres from Chilmark Chocolates
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    3 Bedrm 4 Bath Contemporary - JULY AVAILABLITY-  Ferry Tickets for 7/7 & 7/141 / 23
    (4)Excellent
    2.5 kilometres from Chilmark Chocolates
    3 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Patio
    • Grill
    • Balcony
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 29, 2015
    My wife and I invited two of our former au pairs, another au pair who was their close friend and one of their sisters to have a special reunion with us on Martha's Vineyard over...
    Reviewed September 23, 2015
    I recently spent a week at this wonderful house with a girlfriend. The minute we opened the door, we felt right at home! The home is open and spacious yet warm and comfy. The...
    See all reviews
    About this property
    PLEASE NOTE: AVAILABLE JULY 2018 DATES HAVE BEEN DISCOUNTED AND LENGTH OF STAY HAS BEEN REDUCED TO 5 NIGHT MINIMUM. FERRY TICKETS FOR SATURDAY DATES MAY STILL BE AVAILABLE SO PLEASE INQUIRE. DESCRIPTION: This spacious, well-decorated home is conveniently located at the end of a quiet...
    View all property information
    Location Information
    Vineyard Haven, Martha's Vineyard
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 7
    Make Enquiry
    Oak Bluffs Contemporary Summer Home1 / 18
    (5)Very good
    2.6 kilometres from Chilmark Chocolates
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • DVD Player
    • Grill
    • Parking
    • Cable/satellite TV
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 29, 2017
    The location of this home is great. Just outside of town and easy to get to everything in Oak Bluffs. The host was easy to work with and very gracious. She answered questions...
    Reviewed August 8, 2017
    Excellent location close to hiking trails, MV shuttle, and Oak Bluffs center. Comfortable and clean with plenty of room for our family. We would absolutely recommend this...
    See all reviews
    About this property
    Our comfortable, reverse contemporary home has 2 bedrooms on the first floor (one with a full size bed and one with a twin), a 3/4 bath with shower, as well as a family room with a fold-out futon couch. Upstairs on the second floor, our home has an open design with a bright kitchen/dining/living...
    View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    2.8 kilometres from Chilmark Chocolates
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Parking
    • Washer
    • Cable/satellite TV
    • Grill
    • Internet Access
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Home away from Home! Walk to Sailing Camp! Bright, sunny 3 bedroom Cape style vacation home in Lagoon Heights with great amenities. Fully furnished home with 2 baths, outdoor shower, large deck and private enclosed yard and a wonderful deck for the summer cookouts. Open floor plan with spacious...
    View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Oak Bluffs Retreat1 / 21
    (5)Excellent
    0.5 kilometres from Chilmark Chocolates
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Grill
    • Wi-Fi
    • DVD Player
    • Parking
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    We are very excited that we booked the house again this summer. We were there in 2016 and loved it. The house is very clean and it exceeded our expectation. it is centrally...
    Reviewed 4 weeks ago
    Stayed at a lovely home on the Island..Pleasant grounds with lots of space..Home is in a great location with easy access to every town ..Beachs nearby and a great golf within...
    See all reviews
    About this property
    Welcome to Martha's Vineyard. So many of our guests have returned year after year because they find our property to be centrally located, clean, updated and relaxing. We strive to make our home comfortable, fresh, modern and relaxing. In fact every year we add something new to make our home even...
    View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    1.7 kilometres from Chilmark Chocolates
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This gorgeous, contemporary air-conditioned private home is perfect for your luxurious vacation on the island. It is 2700 sq ft of well laid-out space and sits on 1.4 acres of land in a private wooded area, centrally located, only minutes from downtown Oak Bluffs and beautiful beaches. The...
    View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Enquiry
    0.6 kilometres from Chilmark Chocolates
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Washer
    • DVD Player
    • Waterfront
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Luxury waterfront home with dock, deep water mooring, a private beach as well as deep water access and marina facilities close-by. Enjoy a commanding view of Lagoon Pond with gorgeous westerly sunsets - second to none! This home offers a spacious open floor plan providing a comfortable yet elegant...
    View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    1.5 kilometres from Chilmark Chocolates
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Set in one of the Island's loveliest residential areas with beautiful landscaping, overlooking Sengekontacket Pond. Wonderful pond views from all bedrooms and living area. This spacious three floor house is well maintained and attractively decorated. Full deck across back facing pond. Access to...
    View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    Save time - get the best Chilmark rentals sent straight to your email!
    Get the List
    Beautiful estate w/large lawn made for socializing & kids' play room!1 / 45
    (1)Very good
    2.3 kilometres from Chilmark Chocolates
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Cable/satellite TV
    • Patio
    • Washer
    • Grill
    • Air Conditioning
    • DVD Player
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With a spacious interior ranging from formal to casual, a separate play room for the kids, and a large lawn, this Martha's Vineyard vacation home is a great choice for your next family trip. Located in the town of Tisbury, this home is just a short distance away from the shores of Lagoon Pond,...
    View all property information
    Location Information
    Martha's Vineyard, Massachusetts
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    Make Enquiry
    2.6 kilometres from Chilmark Chocolates
    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Internet Access
    • DVD Player
    • Grill
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Contemporary design, this spacious home has just been updated and features two spacious living areas, 5 bedrooms and 3.5 bath. Designed to accommodate two families the lower level features a large family TV room, two bedrooms and a bath. The main living level has an updated kitchen with double...
    View all property information
    Location Information
    Vineyard Haven, Martha's Vineyard
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    2.8 kilometres from Chilmark Chocolates
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Cable/satellite TV
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Waterfront Cottage - Sweet 2 bedroom cottage with gorgeous views and fronts on the lagoon. Small beach, great area for young children to splash and play, also the lagoon is a favorite with those who love to kayak. Kayak rentals close by and delivered if rented by the week. This cottage is a guest...
    View all property information
    Location Information
    Vineyard Haven, Martha's Vineyard
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    2.1 kilometres from Chilmark Chocolates
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lovely 3 bedroom 3 bath home bordered by a large landscaped yard. The exterior features a shady wrap around porch with porch rockers,a perfect place to relax , read a book and enjoy the peace and quiet of the surrounding area. The back of the house overlooking the large yard has a deck with dining...
    View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    0.9 kilometres from Chilmark Chocolates
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Washer
    • Private Outdoor Pool (Unheated)
    • Grill
    • Cable/satellite TV
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New Listing for 2018 Summer Season! Interior features, main living area, lower level family room, open kitchen and dining area, five bedrooms including two master bedrooms en-suite, two bedrooms on 2nd level that share a hall bath and children's/teen bunk room on the lower level and a bath located...
    View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Make Enquiry
    1.4 kilometres from Chilmark Chocolates
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spacious waterfront home offers spectacular 180-degree Lagoon views, lagoon beach area perfect for launching kayaks and a great play beach area for children. This lovely home boasts all the amenities is just minutes away from the central town areas of Edgartown, Oak Bluffs and Vineyard Haven....
    View all property information
    Location Information
    Vineyard Haven, Martha's Vineyard
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    2.4 kilometres from Chilmark Chocolates
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Cable/satellite TV
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2010 newly renovated, features central AC, all new kitchen, 2 new baths and hardwood floors on the living level. Open kitchen, living and dining areas are flooded with light from the floor to ceiling windows and opens to a large wrap around deck with lovely views of the the lagoon. The master...
    View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    2.5 kilometres from Chilmark Chocolates
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful 3 bedroom cape on a 1/2 acre of landscaped gardens. Large cathedral ceilings in living room and dining room. There are ceiling fans in most rooms and in the main living room, as well as portable fans. Large outdoor deck circling the house with outdoor shower and screened in porch....
    View all property information
    Location Information
    Edgartown, Martha's Vineyard
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    1.2 kilometres from Chilmark Chocolates
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Washer
    • Grill
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New for the 2016 season! Enjoy this wonderful new three bedroom three and half bath home in Oak Bluffs. The first floor has an open concept with a beautiful chefs kitchen, large dining room and family room with TV. The first floor also has a master bedroom en suite with a king size bed and TV....
    View all property information
    Location Information
    Vineyard Haven, Martha's Vineyard
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
    Make Enquiry
    NIEJE - Modern Summer Home,  Newly updated, Perfect Central Location1 / 23
    (1)Excellent
    1.8 kilometres from Chilmark Chocolates
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • DVD Player
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 19, 2014
    Second Heaven was everything I expected and more. It is conveniently located next to one of the main roads yet snuggled into a wooded area that gives you the feel of privacy...
    See all reviews
    About this property
    Enjoy your vacation at 'Second Heaven', newly updated three-bedroom contemporary cape. Conveniently located 3 miles into Edgartown Center and 3.5 miles to State Beach. Adjacent to bike path. Enjoy the summer cottage feel in this tastefully decorated home with all brand new furnishings...
    View all property information
    Location Information
    Edgartown, Martha's Vineyard
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    1.9 kilometres from Chilmark Chocolates
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Washer
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Air conditioning has been added for the 2017 season! Waterview Farm is a private association with wonderful meadow and water views. It is adjacent to Farm Neck Golf and Tennis Club, which is open the public. There is access to Sengekontacket Pond to launch canoes and kayaks from the private...
    View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Make Enquiry
    1.8 kilometres from Chilmark Chocolates
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Internet Access
    • Patio
    • DVD Player
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful Meadow View Farms home, bordered by expansive landscaped yard, peaceful private setting. Association tennis courts just a short distance from the house and Farm Neck Golf and Tennis is just a half mile from the house. Miles of connecting bike paths begin at the entrance to this lovely...
    View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    2.1 kilometres from Chilmark Chocolates
    6 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • DVD Player
    • Internet Access
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Weku House is a luxury, 5,000 square foot home located in the beautiful town of Oak Bluffs on Martha’s Vineyard. Originally built in the year 2000, this home was fully renovated in 2015. Elegantly decorated with designer furnishings and interior appointments, the meticulous attention-to-detail...
    View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 10
    Make Enquiry
    2.1 kilometres from Chilmark Chocolates
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Patio
    • Grill
    • Air Conditioning
    • Internet Access
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Oak Bluffs retreat featuring 18 X 30 foot pool, outdoor patio with sectional sofa seating, spacious dining deck and three levels of luxury living. The outstanding home has been professionally decorated by one of the islands premier decorators. This house is privately situated in an enclave of...
    View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Enquiry
    2.0 kilometres from Chilmark Chocolates
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Internet Access
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lovely Summer Home located in Waterview Farms a private community on the outskirts of Oak Bluffs ******* Sengekontacket Pond, ( saltwater in inlet from the North Shore). This special home boasts beautiful views across peaceful meadows to Sengekontacket Pond and the North Shore beyond. Launch...
    View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    2.6 kilometres from Chilmark Chocolates
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful, spacious contemporary home, just a short walk from the village of Vineyard Haven, Lagoon Pond and bike paths. This home is located on a private, wooded acreage with large fenced in yard, landscaped gardens, and hammock for relaxing. Features include a fully equipped gourmet kitchen with...
    View all property information
    Location Information
    Vineyard Haven, Martha's Vineyard
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
    Make Enquiry
    1.4 kilometres from Chilmark Chocolates
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Patio
    • Internet Access
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious tri-level contemporary home in the desirable Oak Bluffs community of Meadow View Farms. Conveniently located close to downtown Oak Bluffs with easy access to both Vineyard Haven and Edgartown, This home sits at the edge of a multi-acre conservation area with bountiful trees surrounding...
    View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Enquiry
    1.3 kilometres from Chilmark Chocolates
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gorgeous light filled vacation home, tucked away in a private community centrally located just minutes from Oak Bluffs, Edgartown and several beautiful beaches. Privately situated this home features multiple living areas, chef's kitchen and a spacious patio area with outdoor dining Upon...
    View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    Heated Pool, Hottub,AC,WiFi,sleep22, 2 mi to beach1 / 49
    (1)Excellent
    2.0 kilometres from Chilmark Chocolates
    5 Bedrooms, 4 Bathrooms, Sleeps 22 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Cable/satellite TV
    • Washer
    • Patio
    • Grill
    • Internet Access
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This upscale, newly renovated, 4 bedroom home in a quiet neighborhood in Oak Bluffs. You are 2.5 miles from the town center and Inkwell and State beautiful public beaches. This home boasts a large unground back yard pool and hot tub on the mahogany deck. Large outdoor shower. Grill and fire pit...
    View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 22
    Make Enquiry
    2.4 kilometres from Chilmark Chocolates
    2 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Washer
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This welcoming air conditioned waterfront house and guest house is privately set with panoramic water views of Lagoon Pond, Hines Point, the draw bridge, Vineyard Sound and Cape Cod. The main house has a generous open layout with substantial living room, dining, and sitting areas that allow for...
    View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    Holiday Rental House - 2 Bedrooms, 4 Bathrooms, Sleeps 12
    Make Enquiry
    1.6 kilometres from Chilmark Chocolates
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Internet Access
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sure to please, this lovely all new custom Cape is bordered by lawn and tall oaks, and features a spacious open floor plan in the main living level with dormered cathedral ceiling, a spacious loft and modern well equipped kitchen with prep island/breakfast bar. The location is ideal for families on...
    View all property information
    Location Information
    Vineyard Haven, Martha's Vineyard
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    2.0 kilometres from Chilmark Chocolates
    4 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Internet Access
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This whimsical summer home located in Water View Farms, provides a peaceful retreat overlooking wild flower meadows. Launch canoes or kayaks from the private association beach on Sengekontacket Pond, just a short walk from the house. Great waterfront play area for young children at the association...
    View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 8
    Make Enquiry
    1.3 kilometres from Chilmark Chocolates
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Washer
    • DVD Player
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wonderful, spacious, lovingly maintained and attractive home in exclusive setting - family room with fireplace, large formal living room with fireplace, master bedroom with full private bath. Large kitchen and dining area that opens onto wonderful deck. Association tennis and boat landing on...
    View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    1.8 kilometres from Chilmark Chocolates
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Wi-Fi
    • Waterfront
    • Patio
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a beautiful waterfront home with a pool on the Lagoon. Enter through the impressive foyer with waterviews over the pool and lawn. There is a large living room with cathedral ceilings and dining area on the main level. There is a gourmet kitchen with eat-in dining overlooking the pool. The...
    View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Enquiry
    2.4 kilometres from Chilmark Chocolates
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Grill
    • Washer
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to the perfect island getaway at this gorgeous, recently renovated Oak Bluffs home on lovely Martha's Vineyard. Light-filled bedrooms, a playroom, and a huge deck await! Downtown Oak Bluffs is nearby and it's only one mile to the water. If you'd rather remain on the property, you're...
    View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    1.6 kilometres from Chilmark Chocolates
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Grill
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Outstanding vacation home, centrally located to all three down island town centers and multiple public beaches. Set in the Iron Hill Farm Community of homes this lovely home overlooks picturesque,- Little Duarte pond. Extended families will enjoy the multiple living spaces, 4 large bedrooms,- 3...
    View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Enquiry
    2.2 kilometres from Chilmark Chocolates
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Wi-Fi
    • Washer
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Four bedroom Oak Bluffs home located in the Waterview Farm area of Oak Bluffs. Adjacent to Farm Neck Golf & Tennis. Access to Sengekontacket pond. Great for kayaking and canoeing. Large house great for an extended family or two small families. The first floor has an open concept living room,...
    View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    0.2 kilometres from Chilmark Chocolates
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    • Internet Access
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to this wonderful and pristine clean three bedroom 2 bath Cape Style. Centrally located with easy access to town centers and public beaches all within a 15 min drive from the house. Biking enthusiasts will enjoy the easy access to bike trails that lead to both towns and many miles of bike...
    View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    1.9 kilometres from Chilmark Chocolates
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Waterfront
    • DVD Player
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious and attractive waterfront Cape Cod style home - features gorgeous views, central A/C, Wi-Fi and 4 TV's. Two large decks and a screened porch provide wonderful spaces for summer relaxation in which to enjoy the waterviews. Kayaking enthusiasts will enjoy the gorgeous scenery and wild life...
    View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    2.4 kilometres from Chilmark Chocolates
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Patio
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located just on the outskirts of Oak Bluffs and overlooking the lagoon this sweet summer home offers walking access to the lagoon for morning swims and is a great area for kayak enthusiasts. The sun filled interior features open living kitchen and dining area with a wall of glass that opens...
    View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    1.3 kilometres from Chilmark Chocolates
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Grill
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This lovely 3 bedroom home features an open floor plan on the living level, colorful decor, window ac in all rooms and a well equipped modern kitchen. The home is nicely situated in quiet neighborhood, on the outskirts of Oak Bluffs, convenient to all three down island towns and beaches and a short...
    View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    1.7 kilometres from Chilmark Chocolates
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Patio
    • Internet Access
    • DVD Player
    • Air Conditioning
    • Grill
    • Waterfront
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A truly spectacular way to spend your time on the island of Martha's Vineyard. Enjoy the good life! Waterfront Lagoon: Gorgeous Contemporary with waterviews from just about every room. Spectacular lighting and a baby grand player piano draw you in, absolutely romantic atmosphere from the moment...
    View all property information
    Location Information
    Vineyard Haven, Martha's Vineyard
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    2.7 kilometres from Chilmark Chocolates
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Patio
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    European-styled cottage is tucked away down a private lane surrounded by private yard with gardens - you’ll feel like you have completely gotten away from it all. The front door opens into a classic Mudroom with an antique wood, stadium bench seat - and then you step into the open and airy Great...
    View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    1.6 kilometres from Chilmark Chocolates
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gracious home features an open, airy floor plan. The large living area with all glass walls opens to a large private deck. Patio furnishings and dining table provide additional space for relaxing and barbecues. Spacious modern kitchen is equipped with all modern amenities. This lovely home is...
    View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    2.4 kilometres from Chilmark Chocolates
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    \n Amenities and Features include...\n \nBeachy Cape -Edgartown, Private Yard, Front and Back Decks, Minutes to Towns and Beaches.
    View all property information
    Location Information
    Edgartown, Martha's Vineyard
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    0.9 kilometres from Chilmark Chocolates
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • Wi-Fi
    • Cable/satellite TV
    • Secure Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful, spacious, 6 bedroom 4 full, 2 half baths set in a quiet and private area of Oak Bluffs, close to Edgartown, Vineyard Haven, area beaches and attractions. This home comfortably hosts extended families with multiple living spaces. The main living level features 2 master bedrooms (one...
    View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
    Make Enquiry
    1.7 kilometres from Chilmark Chocolates
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Grill
    • Washer
    • DVD Player
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This charming home is situated in an idyllic private wooded setting on Sengekontacket Pond, one of the largest salt-water ponds on Martha's Vineyard. Comfortably furnished, it has a newlyr renovated kitchen and a new dining area overlooking Major's Cove. There is also a new screened in sun room for...
    View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    2.4 kilometres from Chilmark Chocolates
    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • DVD Player
    • Waterfront
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Architect designed, luxury waterfront retreat. This unique home sits overlooking 500 feet of private lagoon beach and maintains sweeping waterviews up the lagoon. The pool and patio areas feature outdoor dining, sectional sofa seating, lounge area, and a hot tub all taking full advantage of the...
    View all property information
    Location Information
    Oak Bluffs, Martha's Vineyard
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 7
    Make Enquiry
    2.9 kilometres from Chilmark Chocolates
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Private Garden
    • Secure Parking
    • Grill
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minutes to South Beach, Long Point Beach & Downtown Edgartown. Just off the bike path, located in a great neighborhood situated between Vineyard Golf club & Manuel F Correllus State Forest (with public access from our road to miles of hiking trails). A short bike ride to Morning Glory Farm &...
    View all property information
    Location Information
    Edgartown, Martha's Vineyard
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    2.6 kilometres from Chilmark Chocolates
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    • Patio
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    WELCOME TO SANDPIPER COTTAGE, YOUR STYLISH FAMILY RETREAT! COMPLETELY RENOVATED AND NEWLY FURNISHED 4 BEDROOM, 3 FULL BATHROOM CAPE IN A CENTRALLY LOCATED QUIET NEIGHBORHOOD IS READY FOR ITS FIRST RENTAL SEASON. THIS SPACIOUS HOME IS IDEAL FOR THE GATHERING OF FAMILY AND FRIENDS… Four bedrooms...
    View all property information
    Location Information
    Edgartown, Martha's Vineyard
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    1
    List your property
    Owner log in