Pet-friendly vacation rentals in Chatham

5.0 out of 5 average rating, 3 reviews

Luxury Chatham Escape w/ Stunning Waterfront Views

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 water. Sleeping 8, three bedrooms and luxe radiant-heat bathrooms await, while the primary king offers direct deck access. The lower level adds a sectional, TV, game room, and laundry - all with uninterrupted water views. Just minutes to Jackknife Beach, idealic downtown Chatham, and Chatham Bars Inn.

5.0 out of 5 average rating, 22 reviews

Meadow + Main

Welcome to Meadow + Main – A Boutique Coastal Retreat in South Chatham Nestled between the peaceful Twine Field Meadows conservation area and South Chatham's Main Street, you'll be just a short walk from the Old Colony Rail Trail while some of Cape Cod's most beautiful beaches, restaurants, golf courses, and villages are only minutes away. The home is notably tucked away from the main road and surrounded by mature trees, creating a peaceful and private setting where you can truly unwind.

4.94 out of 5 average rating, 35 reviews

Close to Beach, Dog Friendly, Chatham Cottage

Welcome to our enchanting Cape Cottage in the heart of Chatham, where timeless charm meets modern comfort. 4 minutes from the beach and nestled on a spacious half acre, this newly revitalized and renovated home provides an authentic Cape Cod vacation experience. As you step into our home, you'll immediately sense the true heart and soul of a Cape Cod getaway. Our cottage boasts a warm and inviting atmosphere, perfect for families, couples, or friends seeking a luxurious escape to Chatham.

A functional kitchen features light-colored tile flooring and wooden cabinetry. A double sink is positioned beneath a window, and a stove is located adjacent to a refrigerator. Counter space is available on both sides, with additional storage cabinets visible.

4.9 out of 5 average rating, 63 reviews

Chatham Beach Cottage

Relax with the whole family at this peaceful, quiet cottage that's just .3 miles from the beach! Beautifully maintained 2 BR, 2 full bathroom that includes a queen bed pull out couch. This home has an outdoor shower, central AC and an adorable patio to relax on after a long day at the beach. This cottage has everything you need! Enjoy all that Chatham has to offer from this inviting coastal retreat. Close to Cockle Cove on the Nantucket Sound and just a short distance to downtown.

4.98 out of 5 average rating, 130 reviews

A spacious, modern kitchen area features a large island with a dark base and white countertops, accented by pendant lights above. To the side, an open concept living space includes a comfortable seating arrangement and dining area, with natural light streaming in through large windows.

Home in Harwich

Spacious cottage beach Wychmere < 4 min Central AC

Entire spacious newly renovated modern cottage in Harwich Port. Open concept living room with a large kitchen island. Great space for families ! Bank street Beach and Wychmere Beach Club wedding venue are 4 min drive from us ! We’re very close to Harwich Port downtown with great restaurants. We’re centrally located, close to Chatham, Brewster and Dennis. Freedom Cruise Line ferry to Nantucket at the end of our street. Enjoy the bike trail nearby with rental location if needed.

Guest favorite

A calm freshwater pond is surrounded by lush greenery and tall trees. A float is visible on the water, providing a serene spot for relaxation. Lilypads are scattered across the surface, reflecting the clear blue sky.

Guest suite in Chatham

4.9 out of 5 average rating, 105 reviews

Spacious studio on lovely pond in Chatham

Enjoy this spacious studio apartment on a gorgeous, clean private pond. Separate entrance and lots of privacy; direct access to private freshwater beach, with a lovely float. Kayaks are available so you can enjoy the twin ponds. Note: no actual kitchen, but there is a wet bar with a Keurig and fridge to help start each day nicely. The studio has a King-size bed. In addition to the freshwater pond on the property, numerous bay and ocean beaches are just a 5 minute drive away

Guest favorite

A cozy cottage is framed by tall trees, showcasing a landscaped yard with a mix of grass and small shrubs. The home features a light-colored exterior with dark shutters and a welcoming front porch with steps leading up to the entrance.

Cottage in Chatham

4.93 out of 5 average rating, 196 reviews

Cape Cod Classic Cottage Near Forest Beach

See Cape Cod at its most traditional in this cozy, fully renovated cottage. Get a good night's sleep in the cozy bedrooms with central a/c and blackout shades. Prepare for the day in the clean and bright interior. Pack up your beach chairs and cooler and take a short walk down to Forest Beach. Grab your bike and hop on the Cape Cod Rail trail nearby or take a short drive into charming downtown Chatham. After a day in the sun, unwind in the hammock or enjoy a BBQ on the deck.

A charming cottage exterior is showcased, featuring natural wood siding and flower boxes below the windows. The entrance is framed by shrubs, while a grassy area surrounds the cottage. Mature trees provide shade, enhancing the peaceful setting in a tree-filled neighborhood.

4.81 out of 5 average rating, 164 reviews

Delightful Chatham Cottage, Cheerful and Clean

AirBnB Superhost, local owner has 25 years of online vacation rental experience with this property. Refreshed and updated , our 1 bedroom cottage is an ideal getaway spot for a couple or young family. The cottage is located on a 1/2 acre lot in the geographical center of Chatham, on a private road in a quiet, tree-filled neighborhood. Guests all agree that we have a fantastic location at an affordable price. Enjoy a relaxing stay while being close to everything in town.

A modern kitchen features stainless steel appliances and a tiled backsplash, with a clear view of the adjoining dining area. Soft overhead lighting illuminates the space, complemented by hardwood flooring. A large window allows natural light to enhance the inviting atmosphere.

4.95 out of 5 average rating, 103 reviews

Spacious Pet Friendly Cape, Large Yard

Our home is located in a quiet neighborhood close to beaches, golf courses and bike trails. It is a short drive to Chatham town center and is the perfect location to be close to all attractions but secluded enough to unwind. Take advantage of the outdoors on a new deck and large backyard. Large, mature plants and trees surround the property on three sides. Blackberry, raspberry and blueberry bushes in the backyard provide ripe fruit in the summer months.

4.96 out of 5 average rating, 205 reviews

A charming exterior of the Carriage House features weathered shingle siding and a cupola on the roof. Surrounded by landscaped gardens, the entrance showcases a well-kept pathway and a mix of greenery and blooming flowers, creating a welcoming ambiance.

Home in Eastham

The Sea Captain's Carriage House

The 1840s Carriage House has been beautifully remodeled. The first floor has a living room, dining area, kitchen, and powder room with washer/dryer. The backyard deck has seating for four and a Weber gas grill. Upstairs, the large, elegant bedroom features a king-sized bed, sitting area, reading nook/twin bed, writing desk, and ensuite bathroom with shower. The half acre property offers beautiful gardens for you to enjoy and a delicious outdoor shower.

A sandy beach area is shown, populated with visitors enjoying the sun and water activities. Small boats are visible in the distance, while people are seen wearing casual summer attire. Beach chairs and umbrellas are scattered throughout the shoreline.