
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.

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!

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.

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

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.

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!
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.

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 Chatham cottage rentals
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.

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 Cottage@The Compound Beach Resort Habitat

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

Private cottage green friendly and pet friendly

Charming water-front cottage on Martha's Vineyard!

Beautiful walk to Town, Inkwell and harbor!

Charming Cape Cod Getaway near Beaches

Unique Waterfront Artist Cottage

Coastal Cottage — 7 min walk to private beach

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

Not Your Great Aunt's Island Cottage
Private cottage rentals

Red River Beach Getaway

Renovated Chatham Windmill! Walk to Beach/Town!

Steps to Cape Cod Private Beach!

Private House 1 mile to Seagull Beach.

Martha's Vineyard Getaway Cottage

Cozy Cottage

Walk to Beach - Family Friendly - Fireplace

Cape Cottage - Walk to Beach, Ferries, and Town!
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 $187 AUD 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 and kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
30 of Chatham holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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
- New Silver Beach
- Lighthouse Beach
- Sandy Neck Beach
- Nickerson State Park
- Cahoon Hollow Beach
- Cape Cod Inflatable Park
- Sea Gull Beach
- Popponesset Peninsula
- Scusset Beach State Reservation
- Race Point Beach
- Skaket Beach
- Saquish Beach
- Sandwich Glass Museum
- Bass River Beach
- Nauset Beach




