
Cottage holiday rentals in Chatham
Find and book unique cottages on Airbnb
Top-rated cottage rentals in Chatham
Guests agree: these cottages are highly rated for location, cleanliness and more.

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!

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.

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

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.

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

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

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.
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.

@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.

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.

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.

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
Cottage rentals with a hot tub

Hideout at Water's Edge, 131 North Shore Blvd, #4

Willows Main House

Modern 1 bedroom cottage on 2 acres of waterfront.

Best Little Beach Cottage!

Local Beach+ Fireplace + Hot Tub Under the *Stars*

Lakeside Waterfront House in Harwich: 4+beds, 3bth

The Crab Cottage@The Compound Beach Resort Habitat

The Front Cottage: Waterfront/Dock/Hot tub
Pet-friendly cottage rentals

Beach Cottage, without going over bridges to Cape!

★Waterview ★Pet Friendly ★Kayaks ★Trails ★

Pet Friendly Cape Cod Getaway near Beaches

Coastal Cottage — 7 min walk to private beach

Walk 7/10 mile to Beaches *Summer Fri-Fri* Dogs OK

Ferry (Car) Reservations Available for Summer 2026

Charming Cottage near Beach and Ferry.

LUXHOME★Walk2Beach★Firepit★PetOK★Kingbed
Private cottage rentals

Private Beach-Barnstable Harbor Beachside Cottage

Renovated Chatham Windmill! Walk to Beach/Town!

Memorable Moments Cottage

Cheerful, updated 1-bedroom cottage w/free parking

Cozy Cottage

Walk to Beach - Family Friendly - Fireplace

The Breeze Overlooking Minister's Pond

Cozy cottage in Harwich Port - 100 steps to beach
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 $165 SGD 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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- Cape Cod
- Mayflower Beach
- West Dennis Beach
- East Sandwich Beach
- Craigville Beach
- Duxbury Beach
- Onset Beach
- Coast Guard Beach
- Pinehills Golf Club
- Sandy Neck Beach
- New Silver Beach
- Lighthouse Beach
- Cahoon Hollow Beach
- Nickerson State Park
- Cape Cod Inflatable Park
- Popponesset Peninsula
- Sea Gull Beach
- Skaket Beach
- Race Point Beach
- Scusset Beach State Reservation
- Nauset Beach
- Saquish Beach
- Sandwich Glass Museum
- Bass River Beach




