Cottage vacation rentals in Chatham

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Top-rated cottage rentals in Chatham

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Top guest favorite
An outdoor patio area is surrounded by lush greenery, featuring a round dining table set with wood chairs. A vibrant red umbrella provides shade, while a barbecue grill is positioned nearby. The stone pavers lead to a cozy cottage beyond, framed by flowering shrubs.
Cottage in Dennis Port
4.95 out of 5 average rating, 222 reviews

The Strandloper / Beachwalker Cottage

This very clean and spacious 1 bedroom cottage has AC, is within walking distance to two public Nantucket Sound Beaches and is centrally located on Cape Cod. The vaulted ceilings and ample array of windows gives off natural light and a sense of space. FYI The cottage's name, The Strandloper, the Beachwalker, is a member of an extinct tribe of Khoikhoi Bushmen who lived on seafood gathered along the beaches of Southern Africa. Walking beaches is just as special today as it was a millennium ago.

Top guest favorite
A bright kitchen area is visible, featuring white cabinetry and modern appliances. A small dining table with two wooden stools is positioned near a window. The space is enhanced by natural light and wooden flooring, creating a welcoming atmosphere that connects to an adjoining living space.
Cottage in Dennis Port
4.89 out of 5 average rating, 105 reviews

Oyster Isle-Steps from the Beach!

A perfect seasonal escape, come enjoy the ocean waves and sunshine at this beach retreat! Spend time with family and friends exploring all the Cape has to offer in lively Dennis Port. Located steps from Haigas Beach, nearby playgrounds, ice cream shops, restaurants (Ocean House, Sandbar, Pelham House) and more. This 1 bedroom cottage comes fully equipped with a queen bed, beach essentials, outdoor shower, full kitchen & living space, A/C, parking, just steps from the beautiful Nantucket sound.

Top guest favorite
A single-story home features a gray exterior complemented by blue shutters and a coral front door. A manicured lawn surrounds the house, while a pathway leads from the street to the entrance. Trees provide a backdrop, enhancing the home's privacy.
Cottage in Harwich Port
4.93 out of 5 average rating, 100 reviews

Red River Beach Getaway

South of Route 28 - Nine houses from Red River Beach one of the cape's most family friendly beaches - Harwich's only beach with public non resident parking. 1.5 miles from downtown Harwich, this spacious 3 bedroom 2 bathroom home has a large, open living room with vaulted ceilings. Enjoy dinner on the large back deck, overlooking a private yard, perfect for lawn activities. Other amenities include central AC, outdoor shower, laundry, cable television, WiFi internet and more. Linens included

Top guest favorite
A charming white cottage is surrounded by a well-maintained grassy yard, featuring a stone walkway leading to the front door. The exterior is complemented by large windows adorned with shutters, and a light chimney is visible on the roof, adding to the welcoming curb appeal.
Cottage in Harwich Port
4.85 out of 5 average rating, 119 reviews

Cozy & Bright Cape Cod Cottage- Walk to the beach!

Come enjoy all the Cape has to offer in this peaceful and conveniently located home. Half-mile walk to the ocean! You'll be just five minutes away from both downtown Harwich Port and Dennis Port. Spectacular hiking and kayaking can be found right down the road at Bells Neck and Herring River. With a spacious yard that is perfect for relaxing and a cozy living area, this is the perfect coastal home away from home. The cottage is equipped with central A/C, speedy internet, and an outdoor shower.

Top guest favorite
A cozy living room features a large, light-colored sectional sofa adorned with various decorative pillows. A neutral coffee table sits centrally on a woven area rug. Natural light enters through multiple windows, and a wall-mounted flat-screen TV is visible, enhancing the inviting atmosphere.
Cottage in Dennis Port
4.94 out of 5 average rating, 277 reviews

Walk to Beach - Experience Dennis Beach House - AC

A quaint, cozy, well-decorated & well-equipped Cape Cod cottage located .2 miles away from Sea St Beach and a variety of other bars/restaurants, coffee shops and more. The house sleeps 5 people comfortably and has 1 small bathroom. Kitchen is fully stocked. 4-6 bath towels will be provided. The house has many smart home tech amenities, central air, Temperpedic mattresses, and a lovely & large outdoor space/back deck. First time booking on Airbnb? Save using link: www.airbnb.com/c/brianm30025

Top guest favorite
A charming cottage with a shingle exterior is framed by a vibrant yard. A white picket fence encloses flower beds, and a small patio features an umbrella for shade. A welcoming pathway leads to the front door, surrounded by greenery and a manicured lawn.
Cottage in Chatham
4.97 out of 5 average rating, 279 reviews

Cozy Cottage

Our 3 room cottage in the Old Village is within steps of Lighthouse beach and a 15 minute stroll to town along charming streets. Its location in an ample yard insures comfort and privacy for your stay. The kitchen is equipped for stay-at-home dining. The owners live in a separate house on the property and are ready to provide you with knowledge of Chatham’s history and assist you in your explorations of the town or Cape Cod. The owner welcomes your visit to his art studio on the property

Top guest favorite
Cottage in West Yarmouth
4.96 out of 5 average rating, 251 reviews

Cozy Coastal Cottage With Sprawling Sea Views

Take in endless views of the ocean walking up to this quaint cottage. Here, the pace is leisurely – sip coffee on the deck, watch the sunrise, and swim in the warm waters of Nantucket Sound just outside. We make changes yearly! A new marble bath was just installed! Close by is downtown Hyannis to shop and eat, mini golf, a water park, ferries to the islands, harbor tours, biking, and more. You will be at peace and filled with serenity staying here on Cape Cod. Can't wait to host you!

Top guest favorite
The cozy living room features wooden walls and a cathedral ceiling with exposed beams. A plush sofa and a rocking chair are positioned near a large window, providing natural light. A mounted fish hangs above, while a television is placed across from the seating area.
Cottage in Harwich Port
4.91 out of 5 average rating, 159 reviews

"Coaster" Village Location!

Sweet Cottage just a 1/2 mile to Bank Street Beach and only a block from Main Street. Lovely gardens and landscaping makes it a wonderful retreat setting. Summer months July to August 15 are at least 1 week rentals Saturday to Saturday ,August 15 to end of August 3 night stays or if there is availability as the time gets nearer. Off season, 2 to 3 night stay minimum, I provide linens, coffee and towels for short term rentals. Cottage sleeps 3 adults nicely, 4 if 2 children.

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, 188 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.

Guest favorite
An open living area features a comfortable gray sofa facing a round dining table and chairs. A full kitchen is equipped with modern appliances, including a stainless steel refrigerator. Natural light brightens the space through large windows, complemented by light-colored wooden flooring.
Cottage in South Dennis
4.86 out of 5 average rating, 570 reviews

Beachfront Cottage on White Pond (Marshmallow)

Our Cottage sits directly on White Pond tucked away on acres of private property. Our cottage offers a private beach, deck, outdoor shower, outdoor dining area all while enjoying Cape Cod. White Pond is ideal for swimming, boating and fishing. The bike path and well known beaches are less than 2 miles and near to many delicious restaurants. There is another cottage on this property that sleeps four if you have other guest wanting to join

Top guest favorite
The exterior of a charming two-story cottage is visible, featuring light grey shingles and blue-striped awnings. A well-maintained lawn with colorful flowers and greenery surrounds the house, while a gravel path leads to the entrance. Sunlight casts a warm glow over the scene.
Cottage in South Yarmouth
4.93 out of 5 average rating, 117 reviews

Cape Cod charmer 5 minute walk to Ocean beaches

Your oasis to relax, quite street, private back yard with large deck, gas grill, outdoor shower, breezeway and front deck. About a 5 minute walk to two ocean beaches on Nantucket Sound. Enjoy your morning coffee on a park bench as the sun rises over the ocean. Walking distance via sidewalk to beaches, seafood restaurant, Bass River beach pier and Joshua Baker windmill. Saturday to Saturday weekly rentals from late June to early Sept.

Top guest favorite
A quaint cottage exterior is showcased, featuring a screened door and white shutters. Paved stone pathways lead to a sitting area with a vintage-style bench. Flower pots with vibrant blooms are arranged around the entrance, complementing the lush green lawn beyond.
Cottage in Chatham
4.93 out of 5 average rating, 124 reviews

Chatham Cottage - Quiet and Quaint - Beach-Bicycle

Bicycling and the beach! My cottage is located halfway between the Rails to Trails bike path and beautiful Nantucket Sound.(free parking) It’s also equidistance to Chatham’s charming downtown or Harwichport's shops. It’s quiet setting and peaceful atmosphere calls to those who simply want to relax in the hammock or enjoy a meal on your private picnic table, complete with a gas grill. It's perfect for couples and solo adventurers.

Popular amenities for Chatham cottage rentals

Quick stats about cottage rentals in Chatham

  • Total vacation rentals

    Explore 30 vacation rentals in Chatham

  • Nightly prices starting at

    Chatham vacation rentals start at € 110 per night before taxes and fees

  • Verified guest reviews

    Over 1,700 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Chatham vacation rentals include wi-fi 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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