Compare Vacation Rentals & Airbnb in Chatham, MA

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Chatham, MA vacation rentals
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1379 Rentals and Airbnb in Chatham, MA

Best family friendly Chatham, MA vacation rentals

Among the 1379 accommodations in Chatham, MA, here are the 4 best family friendly rentals

120 M² House ∙ 3 Bedrooms ∙ 8 Guests - Chatham, MA
No reviews

120 M² House ∙ 3 Bedrooms ∙ 8 Guests

house, Chatham
This Chatham dwelling is located 700 metres from Cape Shark clothing Store and 800 metres from Chatham Village Market, offering a peaceful, nature-filled setting with tranquil backyard views.
This three-bedroom, three-bathroom property has a floor area of 120 square metres, sleeps up to eight guests, and includes complimentary linens, bikes, kayaks, a gas grill, and $750 of daily exclusive free tickets to local attractions via the Xplorie partnership.
Stage Harbor, 5br,  Water View Walk Town And Beach - Chatham, MA
10 119 reviews

Stage Harbor, 5br, Water View Walk Town And Beach

apartment, Chatham
This charming house is located in the heart of Chatham, just 2km from attractions like the Atwood House Museum and the Chatham Windmill. It has received excellent reviews from previous guests, highlighting its comfortable and relaxing atmosphere.
The house spans 418 square meters and comfortably accommodates up to 14 guests in its five bedrooms. Enjoy the spacious garden, relax in the jacuzzi, and prepare meals in the fully equipped kitchen with a dishwasher.
Guest House Ocean Whisper - Chatham, MA
9.7 4 reviews

Guest House Ocean Whisper

house, Harwich
Guest House Ocean Whisper is a beachfront property located in Harwich, just 19 kilometres from Wellfleet Bay Wildlife Sanctuary and 19 kilometres from Nauset Lighthouse. The house has received excellent ratings for its location, cleanliness, and overall experience.
This 3-bedroom holiday home spans 112 square metres and can comfortably accommodate up to 13 guests. The property offers a range of amenities, including a fully equipped kitchen, a private balcony, a garden, and parking.
Bird Watcher's Paradise!  Renovated Chatham Home - Chatham, MA
9.9 49 reviews

Bird Watcher's Paradise! Renovated Chatham Home

apartment, Chatham
This Chatham holiday home, located 2.25km from the beach, 0.8km from Goose Pond, and a 6-7 minute drive from Chatham's Main Street and Harwich Port, offers easy access to local attractions.
Sleeping up to 10 guests in 4 bedrooms and 2 bathrooms, the recently renovated property boasts a well-equipped kitchen, garden, fitness centre, and family-friendly amenities including beach toys and a fire pit; high-speed internet and smart TVs are also provided.

Best Chatham, MA vacation rentals with a pool

Among the 1379 accommodations in Chatham, MA, here are the 4 best rentals with a pool

Charming 3-bedroom Condo In Endicott Village At Ocean Edge Resort & Golf Club - Chatham, MA
10 3 reviews

Charming 3-bedroom Condo In Endicott Village At Ocean Edge Resort & Golf Club

apartment, Brewster
This three-bedroom Brewster condo, ideal for families, offers easy access to Cape Cod beaches and the Cape Cod National Seashore, with attractions such as the Cape Cod Inflatable Park and Adventure Chatham at unspecified distances.
The 149 square metre property boasts three bathrooms, en-suite dining areas in each bedroom, a fully equipped kitchen in the main living area and individual bedrooms, and a private patio in each bedroom, accommodating up to eight guests.
Adorable Condo With Patio, Shared Pool, & Hot Tub - Close To The Water - Chatham, MA
No reviews

Adorable Condo With Patio, Shared Pool, & Hot Tub - Close To The Water

apartment, Brewster
This Ocean Edge condo in Brewster, MA, is conveniently located near golf courses and beaches, offering easy access to the town beach and the wider Ocean Edge resort amenities.
This 102 square meter apartment accommodates up to six guests, featuring one bedroom, two bathrooms, a fully equipped kitchen, a patio with a gas grill, and access to resort facilities including swimming pools and a gym.
Luxury Home With Pool, Hot Tub & Water View - Chatham, MA
10 2 reviews

Luxury Home With Pool, Hot Tub & Water View

apartment, Chatham
This luxury residence in Chatham offers direct cove access and water views, located a 10-minute drive from downtown Chatham's amenities and close to Jacknife Beach, Lighthouse Beach, Oyster Pond, and Pleasant Bay.
This five-bedroom, five-and-a-half-bathroom apartment sleeps 12 guests and features a chef's kitchen, central gas fireplace, outdoor shower, and expansive grounds with a heated swimming pool, hot tub, and gas fire pit.
Peaceful Retreat On Chilton Lane - Chatham, MA
No reviews

Peaceful Retreat On Chilton Lane

house, Brewster
This Brewster holiday home, situated on Chilton Lane, is 2.1 kilometres from Ellis Landing Beach and 24 kilometres from Cape Cod Gateway Airport.
The 87-square-metre property boasts two bedrooms, two bathrooms, sleeps nine guests, and includes a swimming pool, Jacuzzi, tennis court, and on-site restaurant and bar.

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Best Chatham, MA vacation rentals with a balcony

Waterfront House On Bucks Creek Marsh With Deck, Dock, & Kayaks - Chatham, MA
9.2 47 reviews

Waterfront House On Bucks Creek Marsh With Deck, Dock, & Kayaks

apartment, Chatham
This luxurious waterside residence in West Chatham offers direct access to Bucks Creek Marsh and Nantucket Sound, with Harding's Beach just 500 meters away.
This impressive 291 square meter apartment sleeps up to six guests and boasts a chef's kitchen, a private dock with kayaks and rowboats, and an expansive mahogany deck perfect for enjoying sunset views over the water.
Cape Escape Chatham 5 Star Beach Chic 5 Min Walk To Beach-newly Renovated Private Retreat Ac - Chatham, MA
10 1 review

Cape Escape Chatham 5 Star Beach Chic 5 Min Walk To Beach-newly Renovated Private Retreat Ac

house, Chatham
This newly renovated private retreat in Chatham is located 500 metres from the beach and 27 kilometres from Forest Beach, with Nauset Lighthouse 24 kilometres away.
This 158 square metre holiday home sleeps 18 guests across three bedrooms and two bathrooms, offering air conditioning, Wi-Fi, a kitchen, barbecue facilities, and complimentary bicycles.
Walk To Pond, Amazing Backyard! - Chatham, MA
8.5 35 reviews

Walk To Pond, Amazing Backyard!

apartment, Brewster
This four-bedroom apartment is located just a short walk from Blueberry Pond and a short drive from other attractions in Brewster. It has received excellent ratings for location, cleanliness, and overall user experience.
The apartment spans 146 square metres and comfortably accommodates up to 10 guests. You'll find a fully equipped kitchen, a spacious backyard with a fire pit, a private sand volleyball court, and a large deck with a pergola, perfect for enjoying the outdoors.
Sand Simeon - Relax, Unwind, Repeat - Chatham, MA
No reviews

Sand Simeon - Relax, Unwind, Repeat

house, Chatham
This Chatham property, situated 26km from Nauset Lighthouse and 27km from the Wellfleet Bay Wildlife Sanctuary, offers convenient access to local attractions and beaches.
This seven-bathroom, one-bedroom house boasts 450 square metres of floor space, comfortably accommodating 27 guests with a private pool, free parking, and amenities including Wi-Fi, a fully equipped kitchen, and a fireplace.

Best Chatham, MA vacation rentals with parking

Best Of Chatham+harwich:3bd/2ba/outdr Shower/deck - Chatham, MA
9.9 17 reviews

Best Of Chatham+harwich:3bd/2ba/outdr Shower/deck

apartment, Chatham
This South Chatham house, ideally located between Chatham and Harwich Port, offers easy access to Forest Beach (2.7km), Red River Beach (3.7km), and Ridgevale Beach (4.2km).
The three-bedroom, two-bathroom property sleeps six, boasting a fully equipped kitchen with stainless steel appliances, a spacious open-plan layout, a furnished deck, outdoor shower, and ample parking, plus beach chairs, bikes and a boogie board are provided for guest use.
Family-friendly Harwich Retreat Near Beaches - Chatham, MA
10 2 reviews

Family-friendly Harwich Retreat Near Beaches

apartment, Harwich
This Harwich property is a 3-bedroom, 2-bathroom flat offering excellent user, location, and cleanliness ratings, situated a short distance from Harwich beaches, local shops, and restaurants.
This accommodation includes a fridge, microwave, dishwasher, air conditioning, garden, parking, a screened porch, and a recreation room, comfortably sleeping up to 6 guests.
Beautiful Home In Orleans. Park, Beach, Lake & Ocean.  Telsa Charge - Chatham, MA
9.8 17 reviews

Beautiful Home In Orleans. Park, Beach, Lake & Ocean. Telsa Charge

apartment, Orleans
This seven-bedroom house is located on a river in Orleans, just 0.16 kilometers from Nickerson State Park and within 5 kilometers of Orleans Bowling Center, Stony Brook Grist Mill, Skaket Beach, and Jonathan Young Windmill. The property has received excellent user ratings, indicating a high level of satisfaction from previous guests.
The house comfortably accommodates up to 26 guests and features a fully equipped kitchen, a garden, barbecue grills, and a terrace. Guests can enjoy stunning river views, relax in the tranquil surroundings, and explore the diverse ecosystem of Nickerson State Park, all within easy reach of Orleans' attractions and activities.
Beachside Bliss: Dog Friendly & Breezy Stay - Chatham, MA
10 7 reviews

Beachside Bliss: Dog Friendly & Breezy Stay

apartment, Chatham
This South Chatham holiday home, situated 1km from Cockle Cove Beach on Nantucket Sound and 0.5km from the Chatham Rail Trail, offers easy access to both the coast and local cycling routes.
The 200 square metre property boasts four bedrooms sleeping eight, three bathrooms, a fully equipped kitchen including dishwasher, plus a private garden, spa, parking, concierge service, air conditioning, and includes $750 worth of Xplorie tickets to local attractions.
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