
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.

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

MODERN COTTAGE W/ BIKES, PADDLE BOARDS & KAYAKS
This newly remodeled, nautically themed cottage includes countless amenities designed for a fun, romantic getaway with all the comforts of home. - Bikes, paddle boards, 2-person kayak, yard games, beach chairs/towels & cooler - Outdoor fire pit and gas grill - Stocked kitchen with quality cookware, organic coffee/tea, water filtration pitcher + more - Organic, vegan, unscented, allergen-free soaps & cleaning products - Extreme COVID sanitation protocols as well as quarterly deep cleanings

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

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.

Upper Cape Cozy Cottage
Simple but cozy cottage on an acre property next to the main house. Moderate sized bedroom and living room. Small kitchen and bathroom. The kitchen is fully equipped for cooking. Air conditioning is a portable unit and only in the bedroom. Games, books, and puzzles provided. There is no cable but a smart TV is included with access to Netflix etc. if you have an account. Outdoor area includes charcoal grill and seating . Large back yard with yard games, basketball hoop and fire pit.
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.

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.

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!

Fall Smores! Close to beach w/modern amenities
Just 5 minutes from the beach, this updated Cape Cod home is perfect for small families seeking a relaxing getaway. Inside, enjoy a remodeled space with modern comforts and cozy charm. Out back, unwind on the patio with a lush lawn and easy-start gas fire pit—great for dinners or s’mores under the stars. Stocked with linens, beach gear, toys, games, Wi-Fi, AC, full kitchen, and grill. Close to Holiday Hill mini golf, ice cream, and seafood shacks!

Unique Waterfront Artist Cottage
Once a horse stable, Lil Rose now sleeps up to five just a short walk from a private beach. PLEASE READ BEFORE BOOKING: Rentals in season (April-October) are only offered by the week (Saturday-Saturday). November rentals are offered with a 4-night minimum. Rentals December-March are offered with a 3-night minimum. Pets are accepted (max 2) but you MUST let us know in your booking request about your pet so that we can prepare the property.

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.

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.
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

Best Little Beach Cottage!

NEW! East End Cottage with Private Hot Tub!

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

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

The Crab House @ The OBC Beach Resort and Habitat

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

Private cottage green friendly and pet friendly

Beach Cottage, without going over bridges to Cape!

Charming water-front cottage on Martha's Vineyard!

★Waterview ★Pet Friendly ★Kayaks ★Trails ★

Bold Oceanfront Cottage w/Pvt Beach ~ Lil Sea Sass

Charming Cape Cod Getaway near Beaches

Walk to beach - firepit - fireplace

Onset beach, Cape code.Private Waterfront cottage
Private cottage rentals

Chatham Beach Cottage 2BR + Loft Walk to the Beach

Renovated Chatham Windmill! Walk to Beach/Town!

Bucks Pond Cottage w/Central A/C & Linens

Walk to Beach - Family Friendly - Fireplace

Holiday Cottage in Charming Dennis Village

Escape to the Cape

Cozy Coastal Cottage With Sprawling Sea Views

Views of Cape Cod Bay, walk to the 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 $170 SGD per night before taxes and fees

Verified guest reviews
Over 1,690 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!
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Mount Pocono Holiday rentals
- The Hamptons Holiday rentals
- Capital District, New York Holiday rentals
- Fitness-friendly rentals Chatham
- Rentals with a firepit Chatham
- Beach house rentals Chatham
- Family-friendly rentals Chatham
- Rentals with a washing machine and dryer Chatham
- Rentals with lake access Chatham
- Rentals with a kayak Chatham
- Rentals with breakfast Chatham
- Luxury rentals Chatham
- Rentals with a fireplace Chatham
- Rentals with outdoor seating Chatham
- Rentals with beach access Chatham
- Beachfront rentals Chatham
- House rentals Chatham
- Rentals with a hot tub Chatham
- Rentals with a patio Chatham
- Flat rentals Chatham
- Waterfront rentals Chatham
- Pet-friendly rentals Chatham
- Rentals with pools Chatham
- Cottage rentals Barnstable County
- Cottage rentals Massachusetts
- Cottage rentals United States
- Cape Cod
- Mayflower Beach
- West Dennis Beach
- East Sandwich Beach
- Craigville Beach
- Duxbury Beach
- Onset Beach
- White Horse Beach
- Coast Guard Beach
- Chapin Memorial Beach
- Pinehills Golf Club
- Lighthouse Beach
- Inman Road Beach
- Nauset Beach
- Town Neck Beach
- Ellis Landing Beach
- Nickerson State Park
- Linnell Landing Beach
- New Silver Beach
- Falmouth Beach
- Scusset Beach
- Cape Cod Inflatable Park
- Corn Hill Beach
- Cahoon Hollow Beach




