Chatham Vacation Rental Homes By Owner

NEW OWNERS!!! NEW TO MARKET!!! Located overlooking Chatham's beautiful Oyster Pond, this home is the perfect location for your vacation. Take advantage of the... Read More

NEW OWNERS!!! NEW TO MARKET!!! Plans underway for complete renovation of Windmill prior to 2022 rental season. Current photos reflect existing interiors. New... Read More

*Cancellation policy at end of property description.* A gem in Chatham! This "Upside Down" split level home is just what the doctor ordered to turn you... Read More

16659 - Riverside: Four Bedroom Home in Quiet Neighborhood w/ Screened Porch & Outdoor Shower! ??????? Towards the back of a quiet private neighborhood sits... Read More

16637 The Driftwood: Spacious w/ Large Outdoor Area, Fire Pit, & Game Tables! Our beautifully decorated, spacious, and impeccably clean home is the perfect... Read More

16617 Skipping Stone: Located on the Rail Trail, less than a mile to downtown, close to beaches and surrounded by ponds! This beautifully updated home is a great... Read More

16661 - Hardings Hideaway: Lovely Updated Cape Home, 1 Mile to Hardings Beach, Screened Porch, Outdoor Shower! This lovely updated two bedroom Cape home is just... Read More

4 Bedroom- 4.5 Bathroom- Sleeps 10 Off-Season for Spring and Fall 3+ Night Stays Permitted: Contact Us for Rates and Booking Complimentary Linens Service... Read More

16644 - Lover's Lookout: Enjoy your best days of summer at our waterfront home located on the private Lover's Lake in central Chatham! Bring or rent kayaks/SUP... Read More

16605 Sea Pine Cottage: This quaint Cape home is located just minutes away from Harding's Beach, a beautiful and popular spot to spend the day soaking in the sun... Read More

16625 Riverside Respite: Gorgeous Waterfront Dog-Friendly w/ Stunning Views & Private Dock Access! Enjoy waterfront living at its finest when you escape to this... Read More

16656 Decked Out Oyster: Calling all water enthusiasts! This stunning home has water views and a floating dock just down the street. Enjoy a swim off of your own... Read More

16665 - Sol Mate: Lovely Chatham Home Near Bike Path w/ Large Grassy Yard, Outdoor Shower, Dog Friendly! This lovely four bedroom vacation home, located on a... Read More

16604 The Hideaway: Less than a mile to one of the best beaches in Chatham! Feel the warm sand between your toes at Cockle Cove beach, just .8 mile walk/bike... Read More

16646 - Sunny-Side-Up: Deeded Rights to Emery Pond, Bike Trails Nearby, Game Room, Deck & Backyard, Fire Pit! ???????Spend a week where the sun always shines at... Read More

16658 - Home Base: Centrally located home features front patio, side deck with fire pit and room for the whole family. Conveniently situated in the middle of... Read More

16613 Maiden Chatham: Close to Hardings & Ridgevale Beach, Game Room, Dog Friendly! Enjoy this beautifully renovated, well appointed home for your Chatham... Read More

16614 Chatham Pearl: Walk to Oyster Pond, minutes from downtown Chatham and beaches! This classic Cape Cod home is located in a quiet neighborhood abutting Oyster... Read More

16664 - Family Tides: Waterfront on Schoolhouse Pond w/ Private Beach Access & Water Views from Every Room! This beautiful waterfront property, located directly... Read More

16612 Salt Breeze Cottage - Wraparound deck overlooking Buck's Creek and Nantucket Sound. 5-minute sandy nature walk to a semi-private neighborhood beach! Enjoy... Read More