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.

Chatham Vacation Rentals

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
    Price
    per night
    $472 Average
    |||
    |||
    $0$1,000+
    Suitability
    More filters
    Travellers to Chatham are booking June dates now. Secure your vacation rental today, and have the perfect trip.
    All 373 Rentals in Chatham
    Sort by:
    Default
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Unique Style Chatham Villager In Heart Of It All1 / 24
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Washer
    • Satellite TV
    • Parking
    • Porch
    • Patio
    • Wi-Fi
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This newly renovated, quaint and charming home is set in the heart of Chatham village. Enjoy the full benefit of being steps away from Main Street, the scenic beaches, and the ocean. There are 3 bedrooms/2 baths and plenty of private outdoor space including an outdoor shower and a fire pit....
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Satellite TV
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2017 Rental Rate: $1500 per week, including the cleaning fee~~Off-Season: $1225 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT A true cottage nestled in the pines! Nicely decorated with nautical theme, with air conditioning to keep you cool. Comfy & Cozy! Lots of...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Washer
    • Air Conditioning
    • Patio
    • Grill
    • Satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2017 Rental Rate $7900 per week including the cleaning Off-Season: $5600 per week, including the cleaning fee Fabulous home with all the bells and whistles, with deeded access to Stage Harbor beach. Professionally decorated, this 4 bedroom home is full of new high-end furniture, fresh paint, and...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
    Make Enquiry
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Air Conditioning
    • Private Garden
    • Wi-Fi
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming 4 Bedroom Cape House in a quiet setting that sleeps 10 (5 queen beds). Two good sized family rooms and a spacious back deck provide plenty of space for the family to spread out (complete with outdoor shower) . Easy walk (~ 10 mins) to two beaches (Forest & Pleasant Street). Additional...
    View all property information
    Location Information
    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Washer
    • Patio
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2017 Rental Rate: $2175 per week, including the cleaning fee Off-Season: $1175 per week, including the cleaning fee Wonderful two bedroom summer rental, just steps to the center of Chatham! Filled with comfortable upscale furnishings, it offers plenty of living space and a great location near the...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Satellite TV
    • Internet Access
    • Grill
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2018 Rental Rate: $7150 per week, including the cleaning fee ~~ Off Season: $4100 per week, including the cleaning fee Luxurious home, with central air and the perfect location! Located steps from Chatham's Fish Pier, you can walk to the beach, or in to town for one of Chatham's famous Friday night...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
    Make Enquiry
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Air Conditioning
    • Patio
    • DVD Player
    • Satellite TV
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2017 Rental Rate ~ $3050 per week including the cleaning fee. ~~ Off-Season: $2200 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT This recently renovated four bedroom beach cottage is in the heart of the beautiful and kid-friendly Hardings Hills area. It offers a...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    Save time - get the best Chatham rentals sent straight to your email!
    Get the List
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Internet Access
    • Patio
    • Satellite TV
    • Washer
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2018 Rental Rate: $5225 per week, including the cleaning fee Off-Season: $3925 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT It is all about location! This spacious 3+ BR home, recently renovated, is located across from Oyster Pond and is a quick walk to everything...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Enquiry
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Satellite TV
    • DVD Player
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bring the whole family to Cape Cod! This sprawling 4BR, 4.5BA home sleeps 15 in comfort. Kids will love the basement entertainment and sleep area, and you’ll adore the 3-season room. Walk to Forest Beach, and drive to downtown Chatham in 10 minutes! INSIDE THE HOUSE From a drive with parking...
    View all property information
    Location Information
    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
    Make Enquiry
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Satellite TV
    • DVD Player
    • Washer
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2017 Rental Rate: $2100 per week, with the cleaning fee ~~No Off-Season~~ Welcome!! This roomy Cape sits up on a hill located just off of Cockle Cove Road on a quiet one way drive. Just .4 mi to Cockle Cove Beach. There are three bedrooms and 2 full and one half baths. The master BR is en-suite...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    Quintessential Cape Cod Vacation Home in N.Chatham1 / 41
    (1)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Patio
    • Washer
    • Balcony
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to the Whydah Figawai - a privately-owned five bed room vacation home in exclusive North Chatham, just a few steps away from the private beach on Pleasant Bay. This traditional Cape Cod home is located in a serene setting and offers the perfect combination of quiet and accessibility for...
    View all property information
    Location Information
    Chatham, Cape Cod 02650
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Washer
    • Air Conditioning
    • Grill
    • Satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2018 Rental Rate: $1650 per week, including the cleaning fee~~No Off-Season Updated and light two bedroom home, on Hitching Post Rd near the ball field and the playground! Great yard for kids to play while you enjoy spending time in the sunroom! It is a short walk to the Rotary at the beginning of...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Washer
    • Internet Access
    • Patio
    • Satellite TV
    • Waterfront
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2018 Rental Rate: $3100 per week including the cleaning fee ~~ Off-Season: $2700 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Boater's Delight!! Beautiful views of Ryder's Cove, a picturesque saltwater inlet in North Chatham. The rental property has a 120' deep-water...
    View all property information
    Location Information
    Chatham, Cape Cod 02650
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Grill
    • Housekeeping Included
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled in a private garden setting a delightful 3 bedroom / 1.5 bath home in Hardings Beach Hills is available to rent this season. With access to Buck's Creek flowing to Nantucket Sound, you can launch your kayak, fish or crab from the private association neighborhood dock and picnic area just...
    View all property information
    Location Information
    Chatham, Cape Cod 02669
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    Pleasant Forest Shores cottages #3 : So. Chatham1 / 14
    (2)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Grill
    • Parking
    • Wi-Fi
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Yes, the price is low but that's why so many customers have come for decades! Looking for a nice clean quiet cottage close to Nantucket Sound beaches? And one that you can afford on a tight budget with some money left for gas & dining? Well, then...Pleasant Forest Shores just may be the place for...
    View all property information
    Location Information
    South Chatham, Chatham 02659 1525
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Patio
    • DVD Player
    • Waterfront
    • Air Conditioning
    • Grill
    • Satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ON THE WATER ...<BR><BR>* Beautiful water views! <BR>* Back decks open to mesmerizing views of Emery Pond <BR>* Hammock and patio furniture chosen for comfort and relaxation!<BR>* Direct access to pond from backyard. <BR><BR>* Clean swimmable pond.<BR>* Bass fishing plentiful!<BR>* Gas grill.<BR>*...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Washer
    • Grill
    • Air Conditioning
    • Satellite TV
    • Patio
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2018 Rental Rates ~~ In Season: $2925 per week, including the cleaning Off Season: $2175 per week, including the cleaning Enjoy all Downtown Chatham has to offer but also enjoy the peace and quiet of staying off the beaten path! This darling rental sits about 1 block from the shops and restaurants...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    5 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Satellite TV
    • Patio
    • Washer
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2018 Rental Rate: $6825 per week, including the cleaning fee ~~ Off-Season:$5325 per week, including the cleaning fee ~~ Weekly rentals from mid-JUNE to mid-SEPT ~~ Lovely home in sought after Stage Neck area! This spacious home offers a private setting on just over an acre of land. It is about 2...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 11
    Make Enquiry
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Washer
    • Air Conditioning
    • Satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2017 Rental Rate: $2150 per week, including the cleaning fee Off-Season: $1525 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Spacious three bedroom ranch in quiet neighborhood near Hardings Beach. Recently updated, it is filled with comfortable furnishings and has...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • Terrace
    • Washer
    • Internet Access
    • Parking
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Featuring gorgeous gardens and outdoor spaces to explore, a luxurious and updated interior, and all the comforts of home, this beautiful rental has it all! Ideal for two guests, this would be a fantastic place for a honeymoon, couples getaway, or even a relaxing solo retreat. Nestled in a quiet...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Washer
    • Patio
    • Satellite TV
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2018 Rental Rate $3875 per week, including the cleaning fee Off Season, $2725 per week, including the cleaning fee Light and bright, this spacious beach home is located right down the street from family-friendly Hardings Beach. Plenty of room to spread out and relax as you enjoy your Chatham...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Washer
    • Grill
    • Ocean Views
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This comfortable and spacious classic Cape Cod-style house is custom-designed and offers bright, open rooms in a secluded, natural setting. Its location is superb: a family-friendly Pleasant Bay beach is minutes away and in the other direction, a large shopping area provides convenient...
    View all property information
    Location Information
    North Chatham, Chatham 02645
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Enquiry
    Pleasant Forest Shores cottages #2 : So. Chatham1 / 9
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Porch
    • Wi-Fi
    • Central Heating
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Yes, the price is low but that's why so many customers have come for decades! Looking for a nice clean quiet cottage close to Nantucket Sound beaches? And one that you can afford on a tight budget with some money left for gas & dining? Well, then...Pleasant Forest Shores just may be the place for...
    View all property information
    Location Information
    South Chatham, Chatham 02659 1525
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Washer
    • Porch
    • Wi-Fi
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Short Drive to Everything! Our cape home offers lots of space for your family. 3/4 mile to Pleasant Bay Beach, 1 minute walk to Ryder’s Cove boat yard, few minutes walk to tennis courts and Cape Cod bike trail. 5 minutes drive to town center. Close to playground and baseball field - home of the...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
    Make Enquiry
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Terrace
    • Balcony
    • Grill
    • Housekeeping Included
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This charming ranch is great for two families. Home has 3 bedrooms plus a bunk room, 2 baths, and is wheelchair accessible. The expanded Master Bedroom, en suite and hallway bathrooms, and kitchen are all newly renovated. The living room and Master Bedroom have new wide-screen HD TVs, and the house...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
    Make Enquiry
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Internet Access
    • Washer
    • Air Conditioning
    • Satellite TV
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2018 Rental Rates ~ In Season: $3675 per week, including the cleaning fee Off Season: $2675 per week, including the cleaning fee Classic Chatham home, recently remodeled, located in the heart of the village and just steps to Mill Pond! Freshly painted, it features new beds, and furnishings...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Walk to Chatham Main St., boutiques, restaurants, galleries, and nightlife! Welcome to The Chatham Bars Carriage House, located within walking distance to Historic Main St. with it's endless variety of boutiques, restaurants, galleries, and nightlife! Enjoy this traditional, yet well-appointed...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Amenities & Details
    • Terrace
    • Grill
    • Wi-Fi
    • Satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Take in panoramic views of the shimmering Atlantic from this 4-bedroom, 2-bath luxury house beside a beautiful wetlands conservation area. Built on Chatham's highest point, the house has incredible views, a touch of opulence, room enough for 8, and is just a 2 minutes from gorgeous ocean beaches...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Satellite TV
    • DVD Player
    • Grill
    • Washer
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2018 Rental Rates: $3375 per week, including the cleaning fee Off Season: $2275 per week, including the cleaning fee Walk to town in minutes from this recently updated ranch on Highland Avenue! Light and bright with new furnishings throughout, this adorable home features wireless internet, central...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Satellite TV
    • DVD Player
    • Washer
    • Parking
    • Grill
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lovely, renovated and very clean. Two-full bath condo near Ridgevale Beach. No roads to cross to access the beach road. Full kitchen and dining; Enjoy the private patio area with weber grille overlooking lovely plantings and lawn area. air conditioning , comfortable furnishings, and child...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Satellite TV
    • Patio
    • DVD Player
    • Air Conditioning
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2018 Rental Rate: $2775 per week, with the cleaning fee ~~September: $1925 per week, including the cleaning fee~~ Take advantage of the quick walk to the Chatham A's Ball Field, the playground and Main Street from this pristine three bedroom ranch! There are two living spaces, great for the kids...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Spectacular Waterfront Townhome - Oyster Pond #311 / 13
    (9)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Wi-Fi
    • Grill
    • Outdoor Dining Area
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    OYSTER POND AT CHATHAM consists of 32 privately owned townhomes set on 17.5 acres on beautiful Oyster Pond in Chatham, Cape Cod, Massachussetts. Beautiful two bedroom plus a den and a loft, two and a half bathroom townhome with gorgeous direct water views of Oyster Pond. Beautifully decorated with...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Washer
    • Satellite TV
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2017 Rental Rate: $2375 per week, including the cleaning fee ~~Off-Season: $1675/week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Light and bright cottage just steps to the warm Nantucket Sound waters of Pleasant Street Beach! Tasteful, traditional furnishings throughout....
    View all property information
    Location Information
    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Captain's Haven1 / 16
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Garden
    • Grill
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    An old-fashion Cape vacation set in a secluded village of quaint, privately owned cottages on 4 acres of pine forest located on White Pond. This true Cape cottage is ideal for a couple or a small family. It has a complete kitchen/ living area with a pull out sofa bed, one bedroom with 2 twin beds...
    View all property information
    Location Information
    West Chatham, Chatham 02633
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Satellite TV
    • Grill
    • Washer
    • Internet Access
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Convenient Location, Near Riverbay in Chatham! Open floor plan living, central A/C, 3 bedrooms and 2 bathrooms are just the beginning of what this property offers. Enjoy relaxing on the deck after exploring nearby East Harwich and Chatham. $1500 per week * $100 Handling Fee * Choice of $55...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Washer
    • Internet Access
    • DVD Player
    • Parking
    • Grill
    • Air Conditioning
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    16 SEA STRAND LANE (ID#109551) CHATHAM Charming and comfortable! Located in a quiet area within a short driving distance to both Hardings and Ridgevale Beaches. Air conditioning cools the home with units in every bedroom, including first floor master bedroom. WiFi, outdoor shower, washer/dryer,...
    View all property information
    Location Information
    West Chatham, Chatham 02669
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Satellite TV
    • Washer
    • Air Conditioning
    • Parking
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    52 PLEASANT STREET Easy access to Pleasant Street Beach! This house is close to South Chatham restaurants, Pleasant Street Beach, the Cape Cod Bike Trail and it is just a short drive to both downtown Chatham and Harwich Port. 3 bedrooms and 2 bathrooms allow for a comfortable living set up....
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    15 Bobbies Lane 430701 / 14
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Internet Access
    • Parking
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    15 Bobbies Lane CHATHAM Charming and Updated Cottage in South Chatham! A/C, convenient to shopping, beaches, and golf. Only 1/2 mile to Nantucket Sound. Screened in Porch, WiFi, 1 Queen, 2 singles and 2 Queen Sofa beds. Sleeps 6. $1250 per week * $100 Handling Fee * Choice of $55 Damage...
    View all property information
    Location Information
    South Chatham, Chatham 02633
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Parking
    • Patio
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    19 Glendon Way, S. Chatham Casual knotty pine summer cottage just 1/2 mile to Pleasant Street Beach. This 3BR/1BA single level cottage is located in a nice quiet neighborhood of South Chatham. Convenient to shopping - just a 10 minute drive into town. $1000 per week * $100 Handling Fee * Choice of...
    View all property information
    Location Information
    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Satellite TV
    • Washer
    • Parking
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    169 Lime Hill Road CHATHAM This magnificent and well-appointed home is the epitome of luxury living with added Cape Cod style. Conveniently located less than 3/4 of a mile from Chatham Village, you also have deeded rights to a path to Oyster Pond.. Every amenity is provided, from central air to...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Parking
    • Washer
    • Internet Access
    • Grill
    • Satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    105 Fox Hill Road (#133951) - Beautiful Home with Fairway Views! Beautiful Home with Fairway Views of Eastward Ho! This lovely home masterfully combines the charm and grace of an antique with the updates and amenities of a newer home. Set on a parcel of land overlooking the Eastward Ho Golf...
    View all property information
    Location Information
    North Chatham, Chatham 02650
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    Make Enquiry
    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Washer
    • Air Conditioning
    • Patio
    • Satellite TV
    • Parking
    • Internet Access
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    105 Queen Anne Road Water views from this beautifully maintained home located just around the corner to downtown Chatham and 1/10 of a mile to the beach on Oyster Pond! All the amenities including central AC, WIFI, outside shower & gas grill. 3 bedrooms each with full baths and a finished lower...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 10
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Parking
    • Satellite TV
    • Air Conditioning
    • Washer
    • DVD Player
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cute cottage only 1 mile to Hardings Beach! 2 bedroom, 2 bath Cape Cod Cottage! Well maintained and appox. 1 mile to Hardings Beach in Chatham. Relax and dine in the screened porch which expands across the front of the cottage. This neighborhood is located off Barn Hill and a short distance to...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Washer
    • Parking
    • Satellite TV
    • Grill
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    64 Waveland Chatham Lovely home in excellent condition located just a short drive to Hardings Beach. This home has been well cared for and features two separate living areas with DVD players, large flat-screen TV s and expanded cable for Red Sox games. The town landing on Oyster River is just...
    View all property information
    Location Information
    West Chatham, Chatham 02669
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Satellite TV
    • Patio
    • Air Conditioning
    • Parking
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    11 JEANETTE DRIVE Just over a mile to downtown Chatham and also close to Hardings Beach and Oyster Pond! This great house is convenient to the bike trail, tennis courts and has deeded rights to a fresh water pond! With four bedrooms and two full baths, this updated home comfortably sleeps up to...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Satellite TV
    • Internet Access
    • Grill
    • Washer
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Well maintained two bedroom home that sleeps 6. One queen and 2 twins with a pullout in the den. Located in scenic North Chatham. A five minute drive from downtown Chatham, Chatham Bars Inn, the Lighthouse, Chatham Seaside Links golf course and the baseball field which hosts the Cape Cod Baseball...
    View all property information
    Location Information
    Chatham, Cape Cod 02650
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Washer
    • Parking
    • Internet Access
    • Air Conditioning
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Schoolhouse Pond just 1/10 mile! Charming custom remodeled Cape Cod home, 1/10 mile to Schoolhouse Pond Beach--perfect for freshwater beach lovers. First floor offers open kitchen / living area with AC unit and one first floor queen bedroom with a ceiling fan. Second floor has three bedrooms all...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
    Make Enquiry
    List your property
    Owner log in