House vacation rentals in Chatham

Find and book unique houses on Airbnb

Top-rated house rentals in Chatham

Guests agree: these houses are highly rated for location, cleanliness, and more.

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Top guest favorite

A spacious house designed in an A-frame style is set within a lush forest. The exterior features large windows and a wraparound deck, surrounded by tall trees and vibrant greenery, creating a serene atmosphere. A pathway leads through the grass towards the entrance.

Home in North Blenheim

4.92 out of 5 average rating, 112 reviews

Think Summer! Hike, Hot Tub, or Relax by the Fire!

Large house perfect for groups & entertaining surrounded by 11 acres near 3 skiing resorts, hiking, state park & more. HUGE WRAP DECK & HOT TUB. 3 Bedrooms & large open loft. Plenty of entertainment space inside & out on 2 floors. New Wood stove, Hi speed WIFI, 2 large TVs, free Prime, Netflix, WII console and plenty of games. Lots to do, day and night inside and out! Beautiful retreat to relax & have fun! Primary and most guests must be over 25 years old,unless family traveling with children.

Top guest favorite

A light-filled living area features large windows with views of the lake. A modern gray sectional sofa is positioned near a circular wooden coffee table, which holds a decorative box. An outdoor patio is visible through sliding glass doors, accompanied by a red umbrella.

Home in Pittsfield

4.97 out of 5 average rating, 115 reviews

Berkshire Lake- Modern and Updated-close to skiing

Lakefront Home for Rent. This home has been 100% remodelled! With a beautiful spot directly on Pontoosuc, the new kitchen, bathrooms, fireplace, and glass enclosed family room all benefit from the idyllic scenery. The home has 5 bedrooms and a convertible playroom with a futon for even more space. 2 bedrooms have bunk beds plus a full size bed in them. 2 bedrooms have king size beds and 1 has a queen. The master suite has an en-suite bathroom and a balcony overlooking the lake. Many upgrades!

Top guest favorite

A spacious retreat is seen from above, featuring a large deck with seating and modern design elements. Surrounding foliage displays vibrant autumn colors, while a gravel pathway leads to the house. The serene landscape emphasizes the property's natural setting.

Home in Round Top

4.96 out of 5 average rating, 195 reviews

Escape in the Catskills w/hottub

Escape to the Catskills: Your Mountain Retreat No Cleaning Fee! Immerse yourself in the breathtaking beauty of the Catskills. Our cozy retreat offers the perfect blend of relaxation and adventure, whether you're seeking a romantic getaway, a peaceful remote work haven, or an exciting outdoor adventure. Unwind in the hot tub while enjoying stunning world-class panoramic views. Conveniently located near charming towns with unique shops, delectable dining options, and hidden antique treasures.

Guest favorite

A two-story home is depicted featuring a stone chimney and large windows, allowing natural light to fill the interior. A wrap-around deck encircles the house, complemented by a well-maintained lawn and nearby trees, providing a peaceful outdoor setting.

Home in Athens

4.92 out of 5 average rating, 118 reviews

Lake house, 700 ft waterfront - from every room

Panoramic views from the wrap-around deck offers privacy and 700 feet of lake frontage from this comfortable home. Enjoy the sunrise and sunsets views of the lake from EVERY room. Two kayaks, canoe, paddle board to be enjoyed from its private beach. The great room has full lake view, heated floors and two large decks. This home offers 4 bedrooms, 2 and 1/2 baths, a finished lower level that features game room with private deck, ping pong table, giant Jenga, home gym, and large 55in TV.

Guest favorite

Home in Kingston

4.92 out of 5 average rating, 251 reviews

This New House Two

Custom built new home built purposefully for Airbnb quests. This house offers a distinctive design with a large loft bedroom and a fully tiled bathroom. The loft overlooks the downstairs living area which has an open living room, dining area, and kitchen. The second bedroom and bath are located on the first floor. Granite, slate, and soapstone accentuate the countertops, vanities, and shower areas. You will also see unique pieces of furniture, accent tables and artwork throughout the house.

Guest favorite

A waterfront home with a unique tower design is reflected in the calm waters of Bantam Lake. The house features multiple outdoor decks, large windows, and is surrounded by trees, providing a serene setting. A private dock extends into the lake, inviting exploration.

Home in Morris

4.87 out of 5 average rating, 149 reviews

Bantam Lake Waterfront Retreat with Private Beach

Waterfront home on Bantam Lake, 3BR/2BA. Relax on the deck, enjoy the sunrise, swim at your private beach. Kayaks available for use (4); bring your boat or jet ski. Minutes away from hiking, snow skiing, vineyards, biking, and so much more. The area offers great restaurants and family friendly activities that are minutes away. BBQ on the gas grill, enjoy the fire pit on the beach. House is great for couples, individuals & families. Please check first if you plan to bring a boat. 7 maximum.

Superhost

A charming two-story blue house is framed by lush greenery and a manicured lawn. Soft light emanates from the yellow windows, creating a welcoming glow. A red door stands as a vibrant focal point, inviting guests into the comfortable space.

Home in Litchfield

4.84 out of 5 average rating, 373 reviews

Rustic - Modern - Hot Tub - Mohawk Mountain - BBQ

Enjoy the comfort of home with air conditioning, heating, dedicated workspace, TV, and Wi-Fi. Cook your meals in the fully-stocked kitchen with all the essentials. Pamper yourself in the private bathtub or shower with provided body soap, shampoo and conditioner. Relax in the hot tub or lounge in the backyard with an outdoor dining area, bbq, patio, and fire pit. 3 Min - Litchfield Town 4 Min - Arethusa Dairy farm 5 Min - White Memorial Conservation Center 16 Min - Mohawk Mountain Ski Area

Guest favorite

A well-lit bedroom features a black wooden bed with a plush blanket layered over crisp white linens. A small bedside table holds a lamp, and framed photos adorn the walls. A window with a blackout shade allows natural light while a wooden chair adds a touch of warmth.

Home in Sheffield

4.91 out of 5 average rating, 117 reviews

Wow! Best BERKSHIRE SnowHome #1 Private SuperClean

"238 Main" has two rentals. Only one rental is rented at a time. Rental #1 has 2 bedrooms, FULLY EQUIPPED KITCHEN and is SUPERCLEAN! (SEE THE 1 BEDROOM LISTING #2!) We are conveniently located between Butternut and Catamount ski stations. Fully renovated, large garden, private entrance, terrace and parking space. Queen size beds. High Speed WiFi. Bathroom has radiant floor heat, towel warmer, plush bathrobes, hairdryer and toiletries. We are in the heart of the Berkshires come visit!

Guest favorite

A charming front porch features white railings and vibrant blue accents. Lush flower beds filled with colorful blooms surround the porch, while a red car is parked nearby. Well-maintained greenery adds to the inviting appearance of the home.

Home in Athens

4.84 out of 5 average rating, 170 reviews

A Victorian "Lady"

Enjoy an old-fashioned vacation right across the street from the Hudson river. Watch the tides, boats, and barges pass by. Dining, kayaking within walking. Historic Hudson, Olana just 10 min. drive. This is a house to relax, use as a base for other activities. It is not intended as a place to party.. It is a quiet neighborhood. I expect my guests to respect that. There is a weekend special. If you book friday/saturday or saturday/sunday the price is $350.00 for the 2 nights. Thanks

Guest favorite

An open dining area features a large, rustic wooden table surrounded by soft, upholstered chairs. Natural light filters through the windows, highlighting a potted plant at the center. In the background, a cozy seating area includes a blue armchair and decorative artwork on the walls.

Home in Catskill

4.94 out of 5 average rating, 109 reviews

Catskill Village House close to dining shops

New for winter 2025 outdoor heated igloo. Quiet street with private parking. Large outdoor deck. Close to Hudson, Hunter and Woodstock. Nearby skiing and hiking. Windham and Hunter ski areas. And north lake. Numerous restaurants, breweries cafes in the bustling Village of Catskill. Short walk to Hudson River and two waterfront parks Need more space. Property is adjacent to https://www.airbnb.com/h/studiocatskillvillage https://www.airbnb.com/h/catskillwaterviewhouse

Guest favorite

Home in Averill Park

4.98 out of 5 average rating, 174 reviews

Lake House in Averill Park, NY (age 30+ excl kids)

Our lake house is on Glass Lake in Averill Park, NY. In case you want to venture off, it is close to Saratoga (race season!), the Berkshires MA, Albany NY, and Vermont. Incredibly private with spacious property. Our lake house is great for families with kids and couples, and handicap accessible. It is great for any season (leaves, skiing, fishing, swimming). Kayaks, row boat.....and the lake!! Age requirement of at least 30 years old for guests (except kids).

Top guest favorite

The charming house features a green exterior with decorative shingles and large windows. A vibrant red tree is situated in front, complementing the landscape. The property is positioned near the water, with a pathway leading to the entrance, inviting guests to explore.

Home in Canton

4.99 out of 5 average rating, 109 reviews

Best River View, on Rail Trail in Collinsville!

This quaint and spotless home is perched on a knoll across the road from the Farmington River & Rails to Trails you can walk to restaurants, gift shops & antique shops; Canoe/Kayak/Paddleboard; go fishing; enjoy the Farmington River Rail Trail; hiking trails, and Ski Sundown close by; or just relax & enjoy the view! Enjoy the best view in Collinsville - one of "America's 10 Coolest Small Towns" by Arthur Frommer's Budget Travel Magazine. Beautiful year round!

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What guests are saying

Spacious, Quiet 4 Bedroom + All Season Hot Tub

4.98 out of 5 average rating, 64 reviews5 days ago

My family had a fabulous 4 night stay at Tina’s place! There was plenty of space to lounge around and we all enjoyed the hot tub. We were a short drive to so many restaurants, farms, breweries and hiking spots. Tina responded immediately every time we asked a question. Would definitely stay here again!

Home in New Paltz

What guests are saying

Modern 4 season lakefront rental

5 out of 5 average rating, 20 reviews6 months ago

An amazing house for a family stay in the Catskills area. Antonia has designed a beautiful home, with so many unique retro nods and details. The basement is an awesome additional space for everyone to hang out in. The backyard set up is also great- with easy access to the hot tub and a few steps to the lake. 15 min drive to great restaurants and things to do-Loved our stay here!

Home in Athens

What guests are saying

Twin Island Lake House • Hot Tub

4.98 out of 5 average rating, 122 reviews3 months ago

Anne Marie's place was exactly what we were looking for! It is extremely well stocked, with everything you might need, from kitchen appliances, extra blankets, many towels, etc. The surroundings were gorgeous and the area is very quiet and peaceful. Anne Marie was friendly and very responsive, answering questions quickly and flexibly. We can't wait to come back!

Home in Pine Plains

What guests are saying

Summer & Leaf Season Rental!

5 out of 5 average rating, 6 reviews3 months ago

What a lovely home! It’s in the residential neighborhood above Great Barrington, which means it’s walkable to Lake Mansfield and the trails there and also either a short drive or a nice walk to everything downtown GB has to offer. The house is squeaky clean with nice kitchen amenities, a yard, and a beautiful detached screen porch for warmer months. Perfect size for a small family and very cozy. We will be back!

Home in Great Barrington

What guests are saying

Real Estate:Therapy - Lake, Laundry, Love it

4.88 out of 5 average rating, 338 reviews1 month ago

Edison’s place was just what me and my friends and family needed for a weekend getaway. It was comfortable and accommodating for the 5 of us and Edison was very communicative. The only thing is to make sure you have a car with good tires as the roads to the house are dirt and very slippery when wet. Otherwise, it was very enjoyable and I would go again given the opportunity.

Home in Becket

What guests are saying

Berkshire Lake House, gunite pool, Chef's Kitchen

4.99 out of 5 average rating, 86 reviews2 months ago

Twelve members of our family stayed here for our annual ski weekend at Jiminy Peak. It was exactly what we needed as our home base -- plenty of room for all of us, good amenities, and the living room gave us a large gathering space where we could all sit after a day of skiing and swap stories, play games, and just enjoy being together. The house was very clean, well-stocked, and the owners were really responsive. We highly recommend it!

Home in Canaan

What guests are saying

Mountain view on Stream beauty

4.83 out of 5 average rating, 120 reviews10 months ago

David’s place is an absolute dream. Like others have said, the pictures don’t do it justice. With the stream in the yard, fire pit, hammock, VHS collection, cozy living room, and lofted bedroom, you could easily spend a week here without going anywhere else. We booked last minute and David was extremly accommodating and quick to respond when we had questions, even going so far as to send me a hand drawn map to help us find our way to a local swimming hole. I’ll absolutely be back! My dogs were bummed to return back to our crammed NYC apartmenr after a dreamy weekend here :)

Home in Phoenicia

What guests are saying

Mountain house + studio

5 out of 5 average rating, 6 reviews3 months ago

My friends and I had a lovely stay in Sarah’s home to bring in the new year together. Sarah was very kind, attentive and responsive! Check in was seamless and the home was just as pictured. A great well equipped & cozy space overall. great location as well and would def recommend to others. thank you sarah!

Home in Elka Park

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