House vacation rentals in Chatham

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Top-rated house rentals in Chatham

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Top guest favorite

A red house with a modern design is shown from the side, featuring multiple large windows that offer views of the surroundings. A gravel driveway leads to the entrance, with a backdrop of rolling hills visible in the distance.

Home in Canajoharie

4.92 out of 5 average rating, 160 reviews

2 homes on large private mountain views getaway

Rent these 5 bedroom 4 bath houses for your next vacation. House sits on top of a hill and has breath taking views, amazing sunrises from the master suite and sunsets from the great room. Home has octagon shape great room with open timber ceiling, large indoor fireplace. Very large and great kitchen for your cooking. Studio has a projector style TV 100 plus inches. Red House/game room with additional 3 queen log beds, full kitchen and bathroom, laundry etc. This home has beautiful open timber.

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, 374 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

Superhost

A secluded riverfront cabin surrounded by lush greenery is showcased. The sturdy wooden deck features outdoor seating, overlooking the river. A stone pathway leads visitors towards the entrance, framed by tall trees and vibrant grass, creating a tranquil setting in nature.

Home in Middletown

4.9 out of 5 average rating, 129 reviews

Riverfront! Swim, Fish, Hot Tub & Game Barn.

Fish, Tube, Hot tub and Game room! All in one property! This exquisite riverfront home has 3 bedrooms and a sleeping loft. This magical property is 7 acres on the River. Bellayre beach 15 mins and Windham mountain biking 30 mins. Hike, s’mores by the fire, hang out in the 3 season game barn equipped with a pool table and darts, have a drink in the riverside hot tub. 5 mins to retro bowling and restaurants. NO FIRST TIME RENTERS ID VERIFIED/REVIEWED RENTERS ONLY.

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!