Cottage holiday 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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Top guest favourite
The serene waterfront scene captures the tranquil reflection of a cottage among lush greenery on a clear day. Trees frame the landscape, with the cottage's features softly mirrored in the still water, creating a peaceful and inviting atmosphere.
Cottage in South Yarmouth
5 out of 5 average rating, 241 reviews

SerenityViews | Waterfront | King Bed | Kayaks SUP

Enjoy our cottage's charm and comfort with panoramic views and abundant sunlight. Comfortably hosts 2 families. Wake up to incredible sunrises. Lounge on the hammock or swim/fish/kayak in our beautiful backyard waterfront Long Pond. Explore the Cape in each direction: beautiful beaches and endless fun activities/interests. At the end of the day, enjoy dining on the deck as you grill. Sit back on the patio with a cocktail and gaze at the star filled sky and ambiance from the fire table. Welcome!

Top guest favourite
The cottage is framed by lush greenery and features a traditional shingled exterior. A welcoming sign reads 'The Strandloper' above the front door. Outdoor seating is provided by adirondack chairs, set on a paved walkway leading to the entrance.
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 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 favourite
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 favourite
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, 278 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 favourite
Cottage in Chatham
4.97 out of 5 average rating, 281 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

Guest favourite
Cottage in West Chop
4.97 out of 5 average rating, 350 reviews

Martha's Vineyard Getaway Cottage

Contemporary cottage on quiet, private, wooded lot. Pristine, bright & comfortably furnished. Open living area, hardwood floors, vaulted ceilings, indoor/outdoor fireplaces, well appointed kitchen, washer/dryer, cable/internet/phone with unlimited national calling, SmartTV with Netflix and additional internet streaming services. Walk or bike to beaches and trails, 5 minute drive from downtown shops and restaurants. Property abuts West Chop Woods with lovely, quiet walking trails.

Guest favourite
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's exterior features a welcoming entrance with a white door and blue shutters. A well-maintained lawn stretches in front, bordered by a gravel path. Two Adirondack chairs are positioned on the lawn, inviting relaxation under the clear blue sky.
Cottage in Dennis Port
5 out of 5 average rating, 120 reviews

@TheCapeSummerHouse - 2bdrm Cottage in Dennisport

Explore Cape Cod from a Beautiful Cottage in Dennisport Village Freshly updated and sunny! This cozy cottage exudes coastal charm. It has a large yard perfect for the kids to play & located just .2 miles to Glendon Beach on Nantucket Sound. It’s a great place to get away for a Cape Cod vacation: central AC, fenced-in backyard with a Weber gas Grill & fire-pit, quintessential outdoor shower, WiFi, Smart TV’s, updated kitchen including a dishwasher, washer & dryer.

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, 172 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.

Superhost
The cottage exterior is framed by trees, with warm light illuminating the windows. A blue umbrella is positioned over a picnic table on the deck, while red chairs add a pop of color. Pathway lights and flower planters enhance the welcoming atmosphere.
Cottage in North Eastham
4.9 out of 5 average rating, 239 reviews

Classic Cape Cod Cottage

No cleaning fee! 15 min walk to the best bayside beach, Thumpertown Beach. The cottage is in a very peaceful wooded setting. A beautiful, charming 2 bedroom cottage 15 min walk to Thumpertown Beach. It's situated on a triple sized lot, close to the outer Cape's favorite attractions. Eastham is known as the Gateway to the Cape Cod National Seashore. Please note, from June 13 to September 6 we have a 7 night minimum from Saturday to Saturday.

Guest favourite
Cottage in South Dennis
4.86 out of 5 average rating, 571 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

Popular amenities for cottage rentals in Chatham

Quick stats about cottage rentals in Chatham

  • Total holiday rentals

    Explore 30 holiday rentals in Chatham

  • Nightly prices starting at

    Chatham holiday rentals start at £96 per night before taxes and fees

  • Verified guest reviews

    Over 1,700 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    30 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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