Cottage vacation rentals in Chatham

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Top-rated cottage rentals in Chatham

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

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Guest favourite
Cottage in Harwich
4.81 out of 5 average rating, 110 reviews

2BR Directly on Pleasant Beach – 30 Steps to Ocean

You are not near the beach- You are on it! Only 30 steps from your door to the ocean! Fall asleep to waves. This is a true beachfront cottage located directly on Pleasant Beach. Drink your morning coffee watching the tide roll in. This adorable cottage is reflective of old Cape Cod and is part of a direct beachfront triplex property in the heart of Cape Cod with panoramic views of Pleasant Beach. You'll never feel like you need to leave the cottage but it is close to the quaint Harwich village.

Top guest favourite
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 favourite
A spacious deck overlooks the beach, featuring two comfortable lounge chairs facing the ocean. The scene captures a sandy shore and distant beachgoers, with vibrant blue skies and gentle waves creating a serene coastal atmosphere.
Cottage in Plymouth
4.9 out of 5 average rating, 100 reviews

Journey’s End Beachfront Cottage with Parking

Escape to the beach and enjoy the Journey's End! This gem of a revived fisherman's cottage is nestled on the beach & provides 180-degree views of unspoiled White Horse Beach on the Atlantic Ocean with uninterrupted views of sea, sky, sunrises, & sunsets. It is THE spot to relax, walk the beach, watch the ships, stargaze, or enjoy a meal oceanside. With its private beachfront deck & beach stairs & one off-street parking space (a rarity), the Journey’s End lives up to its name for vacationers!

Top guest favourite
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, 286 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 favourite
A charming single-story home is presented with light grey shingles and dark blue shutters. A paved pathway leads to the front door, framed by manicured green lawns and landscaped flower beds. Trees and shrubs add to the serene outdoor environment.
Cottage in Harwichport
4.95 out of 5 average rating, 411 reviews

Newly renovated Cape Coddage! Location! Location!

Newly renovated! Harwichport home- 2 min walk to beach, sleeps 10. Located right by Bank St Beach In Harwichport! Walk 1-2 minutes to the beach or walk 1-2 minutes in the other direction to Main Street where you will find shops and restaurants. Ember, The Port, 3 Monkeys, Beer Garden, and Mad Minnow. This home is in the dream location. Pull in and you don't need to drive until you leave. Walkable to Wychmere beach club. This home is often shared by guests of events celebrated at Wychmere.

Top guest favourite
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!

Guest favourite
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.

Top guest favourite
The cottage exterior features a charming white facade with several windows illuminated in warm light. A welcoming front porch is adorned with potted plants, and an American flag is displayed. The surrounding lawn is well-maintained, enhancing the inviting atmosphere.
Cottage in Barnstable
4.99 out of 5 average rating, 173 reviews

Beach Glass Cottage - Pond Front

Come stay at the Beach Glass Cottage! A pristine pond front, completely renovated and tastefully decorated, 3 bedroom, 2 bathroom cottage in the heart of Hyannis. Truly the perfect get-a-way for family and friends. The Beach Glass Cottage is tucked away from the action, but within walking distance to Main Street Hyannis, which features eclectic shops, restaurants, bars, ice cream with mini golf and the Cape Cod Melody Tent is a short walk from the cottage as well.

Top guest favourite
A charming cottage is nestled on a hillside, surrounded by lush greenery. The exterior features a light wood facade and a welcoming front porch with seating. The landscaped yard is manicured, offering a natural setting that blends harmoniously with the surrounding environment.
Cottage in Wellfleet
4.94 out of 5 average rating, 294 reviews

Hillside Cottage

A one-bedroom cottage that sleeps 4, nestled into the hillside at the top of the wetland. Great for birding! Located on a beautifully landscaped property walking distance to Lecount Hollow Beach. The bedroom has a queen bed and there is a queen and a single sleep sofa in the finished basement. There is also a studio apartment available on the premises that sleeps two. The listing name is "Comfortable Studio Apartment".(Pets are allowed in the studio appartment)

Guest favourite
A bright and airy interior space features a light wood table accompanied by two chairs. A comfortable gray sofa is positioned nearby, with decorative cushions adding a touch of color. Large windows allow natural light to fill the room, enhancing a cozy atmosphere.
Cottage in South Dennis
4.88 out of 5 average rating, 469 reviews

Waterfront Cottage on White Pond(Graham Cracker)

Our cottage (Graham Cracker House) sits steps from crystal clear White Pond. The cottage offers private access to the pond for swimming, fishing and boating. The large outdoor space is great for dining and relaxing by the pond. It is 1.5 miles to the Cape Cod rail trail (bike trail), close to many dining options and 3 miles to some of the best beaches Cape Cod has to offer. There is another cottage on the property for rent that sleep 4 guests. No sharks here!

Guest favourite
A light-filled living area features a navy blue sofa and striped accent chairs, complemented by a natural fiber rug. A flat-screen TV is mounted above a white fireplace, with wall art displayed on the blue walls. Windows allow natural light to enhance the space.
Cottage in South Yarmouth
4.9 out of 5 average rating, 134 reviews

Memorable Moments Cottage

Amazing Beach House for Family & Friends. 4 miles to the closest Beach. Beach parking pass available for Barnstable. (9+ beaches and ponds in the Yarmouth area, this parking is not included in the beach pass) Minutes away to great Restaurants, Museums, Mini golf, Ice Cream and so much more. The newly renovated cottage has hardwood floors, updated fully equipped kitchen, Streaming TV, WiFi, high speed internet, and washer and dryer.

Top guest favourite
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 $178 CAD per night before taxes and fees

  • Verified guest reviews

    Over 1,710 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    30 of Chatham vacation 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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