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 Luxury 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
    Location
    Any Distance
    from
    Price
    per night
    C$1,316 Average
    |||
    |||
    C$0C$1,000+
    Suitability
    More filters
    Travellers to Chatham are booking June dates now. Secure your vacation rental today, and have the perfect trip.
    71 Matching Rentals in ChathamView all 474 rentals
    Sort by:
    Price (High to low)
    14 Hallett Lane Chatham Cape Cod - Sand Simeon1 / 48
    (6)Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    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
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    4 bedroom, 3.5 bath Cape Cod Vacation Rental home tucked up off of Bridge Street, in Chatham. BONUS: Linens included !. Privately placed on just over a half acre of land in a peaceful setting, yet just a hop, skip and a jump away you can find Lighthouse beach! It's an easy walk into the village...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    201 Main Street Chatham Cape Cod - Sandpiper1 / 41
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Parking
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience the Sandpiper! Pet Friendly! 4 bedroom, 4.5 bath Vacation Rental located in the heart of Chatham's historic village!! BONUS: LINENS INCLUDED IN SEASON. Whether you are soaking in the hot tub on the private patio or enjoying an outdoor shower after you've come home from Lighthouse or...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come stay at: Donnadune. Pet Friendly! (for dogs only) Waterfront Cape Cod Vacation Rental home in North Chatham on the beach with tennis court. Steps onto the large deck lead you to the entryway of this Cape home. Welcome back in time to when life was more simple-take the time to stare straight...
    View all property information
    Location Information
    North Chatham, Chatham 02650
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    10 Cove Hill Chatham Cape Cod - The Salty Dog1 / 51
    (2)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Hot Tub
    • Wi-Fi
    • Air Conditioning
    • Parking
    • Waterfront
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 29, 2017
    We were looking for a pet friendly place to get away for a long overdue vacation and the Salty Dog fit the bill quite nicely. The pictures cannot capture the beauty of the...
    Reviewed April 3, 2017
    This beautifully furnished, casually comfortable rental feels like home! In an idyllic setting on the water, close to beaches and town, we are in love with the property! Plenty...
    See all reviews
    About this property
    Experience 'The Salty Dog'. Luxury at its finest. This 4,000 square foot, pet friendly, waterfront 4 bedroom/4 bath home sleeps 10. You will find Central Air, free WiFi, linens, and all amenities at this Chatham Vacation Rental Home, everything for a great Cape Cod Vacation! BONUS: LINENS (sheets...
    View all property information
    Location Information
    North Chatham, Chatham 02650
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Air Conditioning
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Lorna Dune! Pet Friendly! A 5,000 square foot luxury 5 bedroom (sleeps 12 with extra bonus room), 5.5 bath vacation rental home in beautiful North Chatham. Walk to beach, Central air, free WiFi, and a heated swimming pool. Coastal comfort & style abound in this spacious home. First...
    View all property information
    Location Information
    Chatham, Cape Cod 02650
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
    388 Main Street Chatham Cape Cod - The Priscilla House1 / 51
    (1)Excellent
    9 Bedrooms, 6 Bathrooms, Sleeps 20 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 31, 2016
    This house was perfect for my group of 6 families with six 13 year old boys and their siblings. Despite the large group, it was incredibly quiet, we didn't get into each...
    See all reviews
    About this property
    Come Stay at: The Priscilla House! Pet Friendly! The Priscilla House is a lovely vacation rental home nestled on Main Street in the charming town of Chatham, Massachusetts on Cape Cod. Walk to town and Lighthouse beach! New Outdoor Space with outdoor kitchen with built in BBQ, comfy outdoor living...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 9 Bedrooms, 6 Bathrooms, Sleeps 20
    5 Bedrooms, Sleeps 11 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Patio
    • Washer
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2019Rental Rates (Cleaning Fee Included): In-Season: $8600 per week Off-Season: $6650 per week Click for More Photos, Map, and Availability Calendar This gorgeous home offers over 5000 square feet of living space spanning three levels, and manages to be both elegant and comfortable. It features...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, Sleeps 11
    Save time - get the best Chatham rentals sent straight to your email!
    Get the List
    5 Bedrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2019 Rental Rate (Cleaning Fee Included): In-Season: $12,950 per week Click for More Photos, Map, and Availability Calendar Fabulous home close to Lighthouse Beach! This gorgeous home offers two en-suite masters, and two more bedrooms, plus a bedroom and full bath in the apartment above the garage....
    View all property information
    Location Information
    Chatham, Cape Cod 2633
    Holiday Rental House - 5 Bedrooms, Sleeps 12
    Chatham Cape Cod Vacation Rental (13199)1 / 26
    (1)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 23, 2019
    Great location with ocean view - accommodated our group of 9 fairly well. Older home with modern, updated interior.
    See all reviews
    About this property
    **SPECIAL** Starting June 1st- June 15th any 4 nights * $2,800 including all fees and taxes $9,400/week Peak Season (7/27 - 8/16) $9,200/week Shoulder Season (Weeks of 7/20 and 8/17) $8,900/week Shoulder Season (Weeks of 7/13 and 8/24) $8,400/week Shoulder Season (Week of 7/6) $7,900/week...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    7 Bedrooms, 5 Bathrooms, Sleeps 20 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Historic North Chatham Estate. Sleeps 20, private beach! Linens included and new beds/furniture for 2018 Rents Saturday to Saturday during peak season Two-night rentals available in the offseason   Please click on the 'Virtual Tour' to see a 3D tour of the home 'Shore Acres', an expansive historic...
    View all property information
    Location Information
    North Chatham, Chatham 02650
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 20
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Internet Access
    • Patio
    • Balcony
    • Grill
    • DVD Player
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    One of the most photographed Wind Mill homes on Cape Cod. Classic old world charm, coupled with all modern conveniences located near the beach and town. The Stony Hill Mill, constructed with 100 year old beams, river rock and barn board, is truly Cape Cod at its finest. This large stately home is...
    View all property information
    Location Information
    North Chatham, Chatham 02650
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    4 Bedrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Washer
    • Air Conditioning
    • Patio
    • Grill
    • Cable/satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2019 Rental Rates (Cleaning Fee Included): In-Season: $8,300 per week Off-Season: $6,000 per week Click for More Photos, Map, and Availability Calendar Fabulous home with all the bells and whistles, with deeded access to Stage Harbor beach. Professionally decorated, this 4 bedroom home is full of...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, Sleeps 6
    5 Bedrooms, Sleeps 9 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Patio
    • DVD Player
    • Washer
    • Internet Access
    • Air Conditioning
    • Waterfront
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2019 Rental Rates (Cleaning and Linen Fee Included): In-Season: $7840 per week Off-Season: $5840 per week Refundable Security Deposit - $1500 Click for More Photos, Map, and Availability Calendar This Lovely antique home overlooking the Oyster Pond Harbor has just completed a fabulous renovation!...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, Sleeps 9
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Patio
    • Grill
    • Parking
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This perfectly situated Chatham rental features everything one is looking for in a Cape Cod rental. In the back yard, a stunning heated pool with attached spa awaits. Located close to Shore Road, you and your guests will enjoy the best of being near the ocean and close to Main Street. Stroll to...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Waterfront
    • Grill
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Extraordinary Chatham Waterfront Home.  Private Beach, Sleeps 10 Peak Summer Weekly Rates: $7,500.00 Rents Saturday to Saturday during peak season Linens included Come enjoy all that Chatham has to offer in this newer, upscale home on Morris Island with beautiful views of Stage Harbor and your...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Cape Cod ⭐️/ Chatham ⭐️SLEEPS 20 ⭐️HISTORIC FAMILY ESTATE OVERLOOKING NANTUCKET SO.1 / 8
    (2)Excellent
    9 Bedrooms, 4 Bathrooms, Sleeps 20 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Wi-Fi
    • Washer
    • DVD Player
    • Ocean Views
    • Waterfront
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Southwesterly ocean breezes flow over this HISTORIC family estate built in the 1930?s by Mr. & Mrs. John Peale Bishop, a classmate and best friends at Princeton of F. Scott Fitzgerald and himself a famous writer and poet. The Gatsby sits on 1.3 acres in Chatham overlooking Nantucket Sound....
    View all property information
    Location Information
    South Chatham, Chatham 02659
    Holiday Rental House - 9 Bedrooms, 4 Bathrooms, Sleeps 20
    Chatham  Cape Cod Vacation Rental (11231)1 / 23
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 4, 2016
    Very recently renovated this is a spacious property with everything we (family of four) could want. Big kitchen, diner, comfortable living room and bedrooms and lots of space...
    See all reviews
    About this property
    Located on the Stage Harbor ?loop', this very private, quintessential Chatham 4-acre retreat is surrounded by mature plantings and conservation land. The home has undergone a full renovation maintaining its historic feel without compromising the modern comforts. The spacious kitchen has a large...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    3 Bedrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Internet Access
    • Washer
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2019 Rental Rates: In-Season: $5500 per week No Off-Season Click for More Photos, Map, and Availability Calendar Gorgeous three bedroom home, located just steps to Lighthouse Beach...plus, your very own stretch of private sand on Little Beach! Enjoy views of Chatham Harbor from almost every room in...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, Sleeps 6
    Chatham Cape Cod Waterfront Vacation Rental (2172)1 / 31
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Waterfront
    • Grill
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 8, 2019
    This is a quality home, updated and kept in great shape. This accommodates family and guests who stop by very well. We love the deck which over looks the Chatham Bay and...
    See all reviews
    About this property
    This truly unique, custom built 5 bedroom, 4.5 bathroom home is just steps from Lighthouse Beach. Spectacular views of Chatham Harbor, North Beach and the Atlantic Ocean from every room in the house and direct access to a semi-private beach nestled between Andrew Hardings Beach and Lighthouse...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Chatham Cape Cod Waterfront Vacation Rental (10325)1 / 42
    (7)Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Waterfront
    • Air Conditioning
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 5, 2019
    Property was great for the whole family. With the house and cottage, our extended family stayed the week with comfort and privacy for all. Great lawn area for the kids. Great...
    Reviewed September 14, 2017
    Great property for a large extended family. This is our third year renting this house and every year it gets better. The newly remodeled master bedroom and bath on the first...
    See all reviews
    About this property
    A traditional Cape Cod pond-front compound set on a beautifully landscaped 2-acre lot with lovely views of Black Pond. Enjoy summer breezes while relaxing on one of the many patios around the spacious yard perfect for lawn games, barbeques or simply stargazing. The main home has 4 bedrooms and 3.5...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
    8 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Chatham Family Compound Sleeps 16 , Walk to Public Beach, Pets Considered, Linens Included Rents Saturday - Saturday during peak season Peak Rates $9,900 - $11,000 before tax PLEASE NOTE:  July 4, 2020 is a Saturday To avoid an unpopular rental turnover day on the July 4th holiday, this property...
    View all property information
    Location Information
    North Chatham, Chatham 02650
    Holiday Rental House - 8 Bedrooms, 6 Bathrooms, Sleeps 16
    5 Bedrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Patio
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Washer
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2019 Rental Rates (Cleaning/Linen Fee Included): In-Season: $14,750 per week Off-Season: $11,750 per week (Weekly Rentals Only) Click for More Photos, Map, and Availability Calendar This elegant five bedroom home is located in the heart of downtown Chatham, and keeps the look of its original...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, Sleeps 10
    8 Bedrooms, 11 Bathrooms, Sleeps 16 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Hot Tub
    • Waterfront
    • Grill
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • Parking
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Rising majestically over Eldridge Point, overlooking Oyster River, Harding’s Beach, and Nantucket Sound, this extraordinary estate features the largest private shoreline in Chatham. Watch glorious sunsets while swimming in your infinity edge pool; or cook dinner in the outdoor kitchen while...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 8 Bedrooms, 11 Bathrooms, Sleeps 16
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Washer
    • Cable/satellite TV
    • Parking
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful Home on Main Street in Downtown Chatham! This gracious and comfortable home has all you could ask for and more in a summer vacation home! Located on Main Street in downtown Chatham, this house is ideally situated for enjoying town and beaches and all the rest this area has to offer....
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautifully renovated 1850 Antique home is literally just steps to Andrew Hardings Beach and Lighthouse Beach via a path directly across from the house. This 4 bedroom, 4.5 bath home has 2,500 square feet of living space and views of Chatham Harbor and the Atlantic Ocean. The shops and...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Waterfront
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on its own point within exclusive and private Stage Island, this Chatham home offers both an idyllic setting and modern comforts. Enjoy stunning views over Stage Harbor throughout the home and direct water access from the private dock (boats under 20' can be brought and tied up for your...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
    4 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Cable/satellite TV
    • Grill
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    • Wi-Fi
    • Waterfront
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Robert Paul Properties Luxury collection rental home. Imagine walking through the front door to a stunning view of the Harbor overlooking Chatham Pier and your own heated pool. Relax in the hot tub or sit on the back patio and take it all in. This waterfront vacation home has magnificent views...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 8
    4 Bedrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Waterfront
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2019 Rental Rates (Cleaning Fee Included): In Season: $8,150 Off-Season: $5650 per week Click for More Photos, Map, and Availability Calendar Stunning home located in Chatham's prestigious Stage Island neighborhood. Gaze out at Stage Harbor from almost every room in the house! It features a...
    View all property information
    Location Information
    Chatham, Cape Cod 2633
    Holiday Rental House - 4 Bedrooms, Sleeps 10
    Chatham Cape Cod Waterfront Vacation Rental (2683)1 / 36
    (2)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Waterfront
    • Grill
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 12, 2017
    Chatham Vac Rentals is fantastic- very easy to work with and extremely responsive to client phone calls. Our Chatham house was beautiful!
    Reviewed August 3, 2017
    We stayed here for February vacation and loved every minute of it! The house is absolutely gorgeous with unsurpassed views from almost every room. The gourmet kitchen has...
    See all reviews
    About this property
    Gorgeous water views from every room in this spectacular 4 bedroom, 4.5 bath home overlooking Ridgevale Beach and Nantucket Sound . This beautifully built, custom home boasts multiple living areas and an open floor plan kitchen, living and dining area with hardwood floors throughout. The kitchen...
    View all property information
    Location Information
    Chatham, Cape Cod 02659
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Patio
    • Parking
    • Wi-Fi
    • Private Garden
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you're fond of sand dunes and salty air.....Location, location, location!! New, lovely furnished home in a quaint little Cape Cod village off Main Street. Minute(s) walk to shops, restaurants, movie theater, library, Chatham Bars Inn, Oyster Pond, Claflin Landing and Lighthouse Beach. Won't...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 4 bedroom, 2 bathroom home is nestled in a charming, natural setting in the heart of Chatham's downtown village yet private location at the end of a cul-de-sac. This home is only 1/2 mile to the sparkling blue ocean waters of Andrew Hardings Beach. There is an open floor plan that boasts...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    103 Bellamy Lane1 / 30
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 6, 2018
    5 stars. We had a great family vacation in this house. The pool area is fantastic. The house is clean and comfortable. It was large enough for 10 of us. The kitchen is very well...
    See all reviews
    About this property
    Tucked in the private Cannon Hill setting, this enchanting 4 bedroom, 3 full and 1 half bathroom home with a large 40 x 20 heated salt-water pool offers tons of comfort and is perfect for your summer getaway. Just a short 3 minute stroll away, on the calm waters of Pleasant Bay, a private...
    View all property information
    Location Information
    Chatham, Cape Cod 02650
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • Secure Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the peaceful tranquility of our beachfront house on Cape Cod in Chatham, Massachusetts. Experience picturesque ocean views from every room from the expansive decks.The house is located on the southern side of Cape Cod right on the beach. This is the ideal spot for a leisurely stroll along the...
    View all property information
    Location Information
    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Spectacular Waterfront Townhome - Oyster Pond #251 / 12
    (8)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Air Conditioning
    • Secure Parking
    • Patio
    • Cable/satellite TV
    • Internet Access
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 29, 2017
    Oyster Pond is an amazing spot. Our family had the opportunity to enjoy the 4th of July in Chatham and we selected unit 25 at Oyster Pond! It was the perfect spot for a family...
    Reviewed August 16, 2017
    At the top of our list for vacation rentals in Cape Cod. Our extended family of 8 rents every year in Chatham and this rental is at top of our list. Luxury accommodations - 4...
    See all reviews
    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. This is a stunning four bedroom, four and a half bath spacious end-unit townhouse with spectacular views of Oyster Pond. Unit 25 is the largest...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to this 1801 Sea Captain's House with alluring old-world charm in Chatham for the ultimate Cape Cod getaway! With 5 bedrooms,4.5 bathrooms and accommodations for 10 this vacation rental house is the ideal size for families, friends, or couples traveling together. Whether you're seeking...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Balcony
    • Central Heating
    • Hot Tub
    • Patio
    • Terrace
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for something different this summer? Think outside the box. This amazing, fully loaded, and secluded property in the Riverbay area of Chatham is a self-contained family fun complex. This home has 3 bedrooms (2 queen, 1 full sized Memory foam mattress) all with new furniture, and the...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Chatham Cape Cod Vacation Rental (102)1 / 19
    (1)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 13, 2017
    My family of 5 has been vacationing in the Ridgevale Beach area of Chatham for many years now. Chatham is our favorite town on the Cape, and Ridgevale is the most family...
    See all reviews
    About this property
    Spectacular 3+ bedroom, 3.5 bath home in one of the most sought after vacation spots on Cape Cod and less than 200 feet to Ridgevale Beach. Breathtaking views of Nantucket Sound from every room in the house as well as the screened-in porch and 1st and 2nd floor decks. Use of semi-private bridge...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Waterfront
    • Grill
    • Hot Tub
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious Custom Chatham Home Plus Guest Cottage with water views NEW for 2019 -- Heated salt-water pool, outdoor kitchen and spa! Linens included, fully updated during 2018 season Rents Saturday to Saturday in peak season This immaculate custom home features 3 master en suite bedrooms and is set...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
    Spectacular Waterfront Home - Oyster Pond 31&321 / 28
    (2)Excellent
    4 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Children's Pool
    • DVD Player
    • Internet Access
    • Cable/satellite TV
    • Hot Tub
    • Waterfront
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 17, 2014
    The house was incredible. I have rented homes across the world with our family, and we are extremely picky in terms of 1. Cleanliness 2. renovation/newness 3. Location 4...
    Reviewed July 17, 2014
    The units we rented at Oyster Pond exceeded our expectations. These two units (31 & 32) were very well appointed with TVs in every room, modern appliances, comfortable...
    See all reviews
    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. Incredible four bedroom, five and a half bathroom double end townhouse with gorgeous direct water views of Oyster Pond. Townhomes 31 and 32 are rented...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 12
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This gorgeous 3 bedroom, 3.5 bath custom home is located less than 300 feet from Ridgevale Beach by neighborhood footbridge. This lovingly detailed and beautifully appointed home features both first and second floor master bedrooms, three living areas, a gourmet kitchen with a piano shaped island,...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Washer
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a truly beautiful home situated in the sought after Hardings Beach community. There is a path leading from the backyard directly to Hardings Beach. This well appointed home has multiple living areas making it easy to gather together or to enjoy some quiet time reading and relaxing. The...
    View all property information
    Location Information
    Chatham, Cape Cod 02669
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    5 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • DVD Player
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • Housekeeping Included
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Only 4 miles from popular Chatham town center with its many shops and eateries, this house sits along the lovely private Eastward Ho! golf course with rolling hills and nearby Pleasant Bay. Also, 5 miles to the north is Orleans center. A large semi-circular driveway swings behind tall oaks and...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 16
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Terrace
    • DVD Player
    • Grill
    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    4 Bedroom, very bright, beachy home with SEPARATE guest house! This home comes equipped with AC, fully stocked kitchen and deck to enjoy your wine/coffee. Not to mention a private enclosed lawn to relax or play on. Located in the HEART OF TOWN. Walk out the driveway and you will find yourself...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    5 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Chatham Resort Feel: Sleeps 16, Heated Pool/Spa, Renovated, Roomy, Upscale. Rents Saturday to Saturday in peak season Linens Included Please click on the 'Virtual Tour'tab to take a 3D tour of the home Just off the historic Chatham “Loop,” this spacious (4,300+ sq. ft.), newly renovated,...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 16
    1 Bedroom, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Washer
    • Air Conditioning
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful, Spacious and Bright Home in North Chatham! This lovely home is located in the Canon Hill Association area of North Chatham and has a private association beach on Pleasant Bay just a short ways down the road! With 4 bedrooms, 3 full baths, 2 half baths and many different living spaces,...
    View all property information
    Location Information
    North Chatham, Chatham 02650
    Holiday Rental House - 1 Bedroom, 4 Bathrooms, Sleeps 8
    South Chatham Cape Cod Waterfront Vacation Rental (1841)1 / 19
    (2)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Waterfront
    • Washer
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 14, 2019
    Nice beach outside your door, shallow cove, no seals/sharks.House not fancy, which works well for the Cape. Has everything you need though...
    Reviewed August 2, 2017
    Great location right on Nantucket Sound. Upstairs you'd think you were on a boat; the water's THAT close. Lovely and very well equipped cottage. Kitchen was recently and...
    See all reviews
    About this property
    Spectacular panoramic water views from this 4 bedroom, 2 bath Chatham rental situated right on Cockle Cove Beach on Nantucket Sound. This is one of very few homes where you can step out your door and take only a few steps to the water's edge. The living room, dining room, kitchen and a full...
    View all property information
    Location Information
    Chatham, Cape Cod 02659
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Grill
    • Waterfront
    • Parking
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful Home on Morris Island! This exquisite property is set facing Monomoy on Morris Island in Chatham. Beautiful water views from every room set the tone for a relaxing and peaceful retreat. The interior is bathed in natural light and with 4 bedrooms and 3 1/2 bathrooms has plenty of space...
    View all property information
    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    1
    List your property
    Owner log in