2 Br Private Vacation Home Vacation Rental In Chatham, Massachusetts
Retreat to the heart of Cape Cod in this restored Cape salt box cottage with 2 bedrooms, offering 1 queen and 2 twins. Starry Hill Cottage combines elements of old Cape Cod with modern finishes and...
Created Jul 20, 2026
3 Br Private Vacation Home Vacation Rental In Chatham, Massachusetts
Wake up to stunning waterfront views at this beautifully designed Chatham retreat. The main level features an open living, dining, & kitchen space with double sliders to a deck overlooking the...
Created Jul 20, 2026
3 Br Private Vacation Home Vacation Rental In North Chatham, Massachusetts
2024 Rental Rates:In-Season: $11,000 per week, Plus Fees and TaxesNo Off-SeasonClick for More Photos, Map, and Availability CalendarGorgeous home with marsh views, plus a pool and hot tub in...
Created Jul 20, 2026
5 Br Private Vacation Home Vacation Rental In North Chatham, Massachusetts
'The Bluff House' is a very private turn of the century informal home located down a private country lane directly on the water overlooking Pleasant Bay, Nauset Beach, and the Ocean beyond. An...
Created Jul 20, 2026
5 Br Private Vacation Home Vacation Rental In Chatham, Massachusetts
Located just 1 mile from the fish pier and CBI, and 1.5 miles to downtown, we are close to all the best Chatham has to offer! From the circular shell-covered driveway to the cedar shakes and...
Created Jul 20, 2026
5 Br Private Vacation Home Vacation Rental In Chatham, Massachusetts
Summary:16696 - Kingdom on the Cove: Luxury Home with Pool, Hot Tub & Water ViewsThe Space:Discover a serene and luxurious escape at this luxury Chatham homea five-bedroom, five-and-a-half-bath...
Created Jul 20, 2026
4 Br Private Vacation Home Vacation Rental In Chatham, Massachusetts
Enjoy your vacation at this lovely North Chatham home. This charming, sunny and spacious, arts and crafts bungalow is completely renovated with hardwood floors throughout. The light and airy...
Created Jul 20, 2026
3 Br Private Vacation Home Vacation Rental In Chatham, Massachusetts
Built in 1920, Lucy's Cottage is located in a quiet and prestigious North Chatham neighborhood and an easy stroll to three town landings - Scatteree (.2 miles), Cotchpinicut (.4), Cow Yard (.7)....
Created Jul 20, 2026
3 Br Private Vacation Home Vacation Rental In North Chatham, Massachusetts
This lovely cape with 3 bedrooms and 2 1/2 baths sits privately on over an acre of land. A classic, antique home filled with new and updated furnishings. Tons of family space filled with light....
Created Jul 20, 2026
3 Br Private Vacation Home Vacation Rental In Chatham, Massachusetts
Summary:Breathtaking architecture, soaring windows, and serene surroundings just minutes from downtown Chatham and world-class beaches.The Space:Welcome to Marshlight Retreat, a breathtaking, sun-...
Created Jul 20, 2026
3 Br Private Vacation Home Vacation Rental In Chatham, Massachusetts
This is a 5* Exceptional property but all its past reviews did not convey when it was recently relisted. Highwood Cottage is an owner-managed home offering lovely outdoor amenities such as a...
Created Jul 20, 2026
6 Br Private Vacation Home Vacation Rental In North Chatham, Massachusetts
Summary:16626 - Cape Whidah: Beautifully Renovated w/ Access to Beach!The Space:This gorgeous vacation home, located in a beautiful area of North Chatham, is perfect for large groups of family and...
Created Jul 20, 2026
Cottage Vacation Rental In Chatham, Massachusetts
Studio cottage with queen bed, full bath and kitchenette. Backyard area with brick patio/pergola and grill with an outdoor shower after the beach. Cottage is convenient to shops, restaurants,...
Created Jul 20, 2026
4 Br Private Vacation Home Vacation Rental In Chatham, Massachusetts
New to VRBO! Welcome to your ultimate Cape Cod getaway. Nestled in a highly desirable Chatham area, this newly listed, high-end home perfectly blends coastal luxury with peaceful privacy. You are...
Created Jul 20, 2026
3 Br Private Vacation Home Vacation Rental In North Chatham, Massachusetts
This exquisite ONE (1) family home, Upside Down house, easily compares favorably to ocean front suites at the Chatham Bars Inn for a fraction of the price! Bedrooms first floor, best views upstairs...
Created Jul 20, 2026
4 Br Private Vacation Home Vacation Rental In Chatham, Massachusetts
My family and I live full time in Lexington, MA. We decided to purchase our first vacation home in Chatham, MA in 2008. While the main reason was the proximity to our home near Boston, we also...
Created Jul 20, 2026
5 Br Private Vacation Home Vacation Rental In North Chatham, Massachusetts
This property is professionally managed by Pretty Picky PropertiesStunning Newly Built Custom Compound in Chatham with a Resort-Style AmbianceNEW Listing for 2026!Rents Friday to Friday during peak...
Created Jul 20, 2026
4 Br Private Vacation Home Vacation Rental In North Chatham, Massachusetts
Summary:16651 - Smooth Sailing: Hot Tub, Fenced Yard & Dog FriendlyThe Space:Keep it classy this summer and spend a week at Smooth Sailing! Enjoy a wide array of rare amenities including a Hot Tub,...
Created Jul 20, 2026
5 Br Private Vacation Home Vacation Rental In Chatham, Massachusetts
Summary:16693 - Chatham Homecoming: Luxury Waterfront with Game Room!The Space:Perched above the shimmering waters of Crows Pond and Ryder Cove, this stunning Chatham vacation home invites you to...
Created Jul 20, 2026
3 Br Private Vacation Home Vacation Rental In Chatham, Massachusetts
Welcome to The Tide Watch - our luxurious retreat, perfect for families or a group of friends! This stunning home features high-end furniture, a sparkling pool, relaxing hot tub & game room...
Created Jul 20, 2026
5 Br Private Vacation Home Vacation Rental In North Chatham, Massachusetts
Panoramic Saltwater Views of Nauset Beach, Strong Island, Bassing Harbor and Pleasant Bay with Private Beach* * * * See end of this description for information about included FREE ACTIVITIES...
Created Jul 20, 2026
2 Br Cottage Vacation Rental In Chatham, Massachusetts
Set your clocks back 70 years, and fish for your breakfast from your own dock or row-boat. This setting has been described as the nicest setting in Chatham. Very Private. Bordered by Conservation...
Created Jul 20, 2026
5 Br Private Vacation Home Vacation Rental In Chatham, Massachusetts
My family and i live full time in lexington, ma. We decided to purchase a vacation home in chatham, ma because of the short access from boston. Chatham has all the charm and beauty as nantucket...
Created Jul 20, 2026
4 Br Private Vacation Home Vacation Rental In Chatham, Massachusetts
Amazing views! Enjoy the views of Pleasant Bay out to the ocean and the Outer Beach! This 4 bedroom 3 bath home is spacious and comfortable. Open kitchen and sitting area for family to enjoy...
Created Jul 20, 2026
3 Br Private Vacation Home Vacation Rental In North Chatham, Massachusetts
Private and pet friendly. The bright, open living and dining area features a large slider that leads directly to the back deck with water views just beyond the trees. This rental property includes...
Created Jul 20, 2026
