House holiday rentals in Chatham

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Top-rated house rentals in Chatham

Guests agree: these houses are highly rated for location, cleanliness and more.

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Top guest favourite
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 Port
4.98 out of 5 average rating, 112 reviews

Lg Modern beach& Wychmere, AC, fast WIFI, king bed

Entire spacious newly renovated modern cottage in Harwich Port. Sun filled open concept living room with a large kitchen island. Great for families ! Less than 4 min drive to Red River beach and Bank street Beach. 3 min drive to Wychmere Beach Club wedding venue. Close to Harwich Port downtown. Centrally located, close to Chatham, Brewster and Dennis. Freedom Cruise Line ferry to Nantucket at the end of our street. Enjoy a hike to Harwich Thompson's field Conservation area. Close to bike trail

Guest favourite
The cottage exterior features a light brown facade with white trim, complemented by blooming hydrangeas in shades of blue and purple. A front porch with white railings invites relaxation, while an American flag is displayed. A spacious gravel driveway leads up to the entrance.
Home in Chatham
4.89 out of 5 average rating, 141 reviews

Cute cottage - walking distance to Ridgevale Beach

Retreat to this very quiet and peaceful residential shore neighbored on a dead end street. If LOCATION is what you're looking for, look no further! This year round cottage will serve as a comfortable and relaxing home away from home for your vacation, with walking rights to Ridgevale Beach about 300 yards from the front door. Provided in your home away from home vacation house are linens, towels, fully equipped kitchen, spacious out door shower, 2 roomy bedrooms, & 4 season porch to relax on.

Guest favourite
A charming cottage is surrounded by lush greenery and soft landscaping. The exterior features a light wood shingle design with a welcoming porch and a shaded deck area. Outdoor seating is present, inviting relaxation under the clear blue sky.
Home in Hyannis Port
4.89 out of 5 average rating, 197 reviews

Cottage with private beach in Hyannis Port

Make your Cape Cod trip unforgettable in this Exclusive Harbor Village Cottage located right in Hyannis! Enjoy this recently updated 2-bed, 2-bath vacation home with access to private beach, beautiful outdoor deck, and peaceful ocean views. Follow the beach path 900 feet to the beach! Only minutes from downtown Main Street, the Melody Tent and Hyannis harbor. Whether you spend your days exploring the Cape, sunbathing on the beach, or relaxing on the deck, you will be sure to love this house!!!

Guest favourite
A spacious outdoor area features a circular arrangement of colorful chairs, including blue, red, and green options. The inviting lawn is framed by trees, with a large glassed-in porch visible in the background, providing a seamless connection to the natural surroundings.
Home in Harwich Port
4.93 out of 5 average rating, 111 reviews

Stunning Home in Harwich Port

Welcome to our stunning retreat in charming Harwich Port! This beautiful 4-bed, 2-bath home is the perfect destination for your next getaway. The spacious interior and finished basement are perfect for families or groups and the big fenced-in yard is ideal for outdoor activities, relaxation and pets (please include pets when booking)! A 5 min drive from the beach and downtown, you'll enjoy all that the area has to offer. Book today and experience the best of Cape Cod in this beautiful home!

Guest favourite
A spacious dining area features a long white table adorned with a runner and decorative centerpiece. Overhead, a chandelier adds elegance, while large windows frame views of the water. Natural light brightens the room, complemented by charcoal slate flooring and a cozy seating arrangement nearby.
Home in Chatham
4.95 out of 5 average rating, 298 reviews

Slate House - a modern waterfront getaway

Water front on Frost Fish Creek! This recently renovated 3 bedroom (sleeps 9) 2 bath home is tucked off the road in a private oasis with panoramic water front views from almost every room. The bright open floor plan with fireplace, blue slate floors, high open ceilings to second floor, three pairs of sliders that boast nature, water views, fire pit, and screened in lounge and abundant sunlight. Walking distance to a small private dog friendly beach. Driving distance to many great beaches.

Top guest favourite
A charming beach house with shingle-style siding is displayed, set within a landscaped yard. Two large bushes frame the entryway, and the building features multiple rooflines and skylights. A brick pathway leads to the front door, with trees providing partial shade in the foreground.
Home in Chatham
4.96 out of 5 average rating, 100 reviews

Beachfront Charmer! Newly Renovated.

Steps to a beautiful sandy beach and just a mile to the heart of Chatham! This charming, newly renovated beach house has the amenities you need to make the most of your time with friends & family. Just 300 ft from Little Beach & a 5 minute walk to Chatham Lighthouse and Lighthouse Beach, we've made our new home the perfect place to gather and relax. All BRs and Living room have AC. Grill on the back deck, stroll to town, rinse off in the outdoor shower...this house has it all!

Top guest favourite
A tranquil scene captures a couple seated on a dock, surrounded by tall green grasses. The calm water reflects soft hues of pink and blue from the sunset, creating a serene backdrop of trees across the pond.
Home in Dennis Port
4.96 out of 5 average rating, 218 reviews

Lakefront House/Private Dock/Year Round Hot Tub/AC

Beautiful cottage nestled on a half-acre of waterfront property on Swan Pond. The dock offers direct water access. Available are two kayaks, a canoe and two paddleboards. The kitchen offers beautiful views of the water while you enjoy your morning coffee. Local beaches are just minutes away. Enjoy the hammock, swings, hot tub, grill, outdoor fire pits and cocktails on the deck. Wanderers' Rest is located close to bike trails, boat rentals, movie theaters, restaurants, and bars.

Top guest favourite
A bright living area features large windows overlooking a scenic marshland and ocean view. A cozy cream-colored couch and an armchair are positioned near a glass coffee table, inviting relaxation. Natural light fills the space, enhancing the tranquil ambiance.
Home in Chatham
4.97 out of 5 average rating, 156 reviews

The Osprey Nest - Beach house with stunning views

The Osprey Nest is a classic Cape Cod beach house just steps to the ocean with panoramic views across the protected marsh. A cozy and timeless retreat, with modern amenities and spacious and light-filled rooms. This home has been in my family since the 1960’s and you will feel the warmth and charm the minute you step in the door. The location is perfect for nature lovers but within 10 minutes of stores, restaurants, and charming towns. A perfect base for Cape Cod sightseeing.

Top guest favourite
An outdoor patio area is illuminated softly at dusk, featuring a dining set with a table and several chairs arranged on a patterned rug. Lush greenery and flowering plants surround the space, while lanterns provide a gentle glow, enhancing the tranquil environment.
Home in Mashpee Neck
5 out of 5 average rating, 199 reviews

Cape Cod Cotuit Cottage, 3 Bed Near Beaches

5 star rental Cottage in the beautiful village of Cotuit! This quaint 3-bedroom cottage is perfect for a getaway for friends and family. It is just a short distance to nearby beaches, local market, walking trails, Cape Cod league baseball stadium, shopping and restaurants. Relax on the private patio area and enjoy the peaceful, natural setting. Bring along your dog too!

Top guest favourite
The exterior of the renovated Chatham home features a white picket fence and a gravel driveway. The house showcases a gabled roof and large windows, surrounded by greenery and trees. The clear blue sky above emphasizes the peaceful neighborhood setting.
Home in Chatham
4.91 out of 5 average rating, 196 reviews

Quaint Downtown Chatham Home

This charming and totally renovated Chatham home is on a private road in a downtown neighborhood of exclusive homes. Its ideal location enables you to walk to Lighthouse Beach about (1/2 mile) and 1 block from downtown Chatham. Also, the house is a quick walk to Children's Beach (Oyster Pond).

Guest favourite
A welcoming entrance is framed by a white trellis, lined with dense green foliage. The pathway leads to a charming house with a light-colored facade and a central front door, flanked by outdoor lighting fixtures and neatly trimmed shrubs.
Home in Chatham
4.94 out of 5 average rating, 187 reviews

Close to everything in Chatham

4 bedrooms ( 1 King bed, 3 Queen beds, 2 Twin beds and a Queen sofa sleeper), 2 1/2 baths, sleeps 10, 3 levels of living space, yard and patio, deck bbq, lounge chairs, large patio table with umbrella, outdoor shower and washer and dryer.

Top guest favourite
The charming front exterior of a gambrel style cottage is visible, featuring shingled siding and a symmetrically gabled roof. Flower boxes are positioned beneath the windows, showcasing vibrant plants. A welcoming dark front door is centered, flanked by two tall, lush evergreens.
Home in West Harwich
4.98 out of 5 average rating, 518 reviews

cape cod riverview cottage

This is a 8 year old gambrel style custom Cape Cod shingled guest cottage is surrounded by lush landscaping and a beautiful view of a tidal river. The river leads to the ocean and is available for canoeing, sailing and kayaking.

Popular amenities for house rentals in Chatham

When is the best time to visit Chatham?

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Avg. price$472 SGD$463 SGD$427 SGD$463 SGD$514 SGD$637 SGD$812 SGD$784 SGD$550 SGD$463 SGD$496 SGD$511 SGD
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Quick stats about house rentals in Chatham

  • Total holiday rentals

    Explore 450 holiday rentals in Chatham

  • Nightly prices starting at

    Chatham holiday rentals start at $103 SGD per night before taxes and fees

  • Verified guest reviews

    Over 12,110 verified reviews to help you choose

  • Family-friendly holiday rentals

    430 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 170 rentals that welcome pets

  • Holiday rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    250 properties have a dedicated workspace

  • Wifi availability

    440 of Chatham holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chatham rentals

  • 4.9 Average rating

    Chatham stays are highly rated by guests – averaging 4.9 out of 5!

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