Vacation home rentals in Western Massachusetts

Find and book unique vacation home rentals on Airbnb

Top-rated vacation home rentals in Western Massachusetts

Guests agree: these vacation home rentals are highly rated for location, cleanliness, and more.

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Guest favorite

A welcoming front porch is adorned with soft, ambient lighting and a decorative wreath. Two rocking chairs sit invitingly beside a wooden sign stating 'WELCOME,' creating a cozy entryway. Light from the interior softly illuminates the space, providing a sense of warmth.

Vacation home in Albany

4.94 out of 5 average rating, 158 reviews

Spacious Urban APT w/4BR & Office in Albany

Visiting Albany for work, vacation, or to visit family? The Twitchell Estate is a spacious 4BR home that will be perfect for your stay. This elegantly designed Boho Chic rental comes with amenities such as self-check-in, Netflix, Disney+, Apple TV, and many other streaming options if you're looking to relax indoors, and a private laptop-friendly office with Wi-Fi if you need to get work done. Enjoy free coffee and tea in the stocked kitchen, with everything you need to feel like you are at home.

Top guest favorite

Vacation home in Warren

4.98 out of 5 average rating, 161 reviews

Private new house on 10 acres of pristine nature

Brand new home! Bring friends and family to this private and stylish place. House provides everything you need for a comfortable and peaceful stay. Fully equipped kitchen, inviting living spaces, large front and back yards with many exploring trails and a pond a few steps away from the house. Close to many 5 star restaurants, wineries, galleries and shops. Hiking, swimming, boating, skiing just to mention a few outdoor activities Close by: Kent School Mohawk Ski Area Lake Waramug High Watch

Guest favorite

An open living area showcases high wooden ceilings with skylights, allowing natural light to fill the space. A simple seating arrangement includes a dark sofa and stylish chairs, while a light rug anchors a coffee table. Modern decor complements the neutral color palette.

Vacation home in Torrington

4.95 out of 5 average rating, 203 reviews

Modern/Private Five ★ /Hotel quality stay/1 BR Apt

Enjoy the comfort and tranquility of this modern apt. A lovely space to relax after a busy day. This clean and bright apt offers a tranquil residential vibe alongside quick, easy access to the Torrington downtown areas, restaurants, stores and bars. It features an open-concept layout, a neutral color scheme, wood surfaces, tasteful furnishings and decor. Designed comfortably for your stay offering WiFi, Netflix, laundry, queen bed, well equipped kitchen, and clean fresh white bed sheets.

Superhost

A spacious bedroom features a light grey bed with simple bedding. A colorful wall art piece adds character to one side, while a desk and chair occupy the other. Natural light filters through the large window, and warm wood flooring complements the overall design.

Vacation home in Hudson

4.85 out of 5 average rating, 128 reviews

Bright and Airy 2 blocks from Warren ST eb

Experience comfort and convenience in this Hudson apartment, perfect for solo travelers, couples, or small families. Enjoy the cozy ambiance of this space, complete with a fully equipped kitchen, and organic washing and cleaning products. You'll find comfortable sleeping arrangements, as well as Smart TV and board/card games for your entertainment. Unwind on your private patio. Whether you're here for business or leisure, don't miss out on this spacious, bright, peaceful space.

Guest favorite

Vacation home in Highland

5 out of 5 average rating, 31 reviews

Charming Vacation House w/ Pool & HotTub

Come and Enjoy this House in the Hudson Valley with serene bedrooms & bathrooms, a huge balcony off the master suite with a huge spa tub overlooking the in-ground pool & orchard. The large living room has an inviting stone fireplace, a gourmet kitchen w/ the commercial range, and floor to ceiling doors that opens to the patio & heated pool. Minutes to Hiking, Biking Trails, Farms, Wineries, Breweries & Great Restaurants & Bars. ****Must be the age of 25 to book; ID REQUIRED****

Top guest favorite

A wooden interior space features a cozy seating arrangement with two armchairs and a sofa. A glass coffee table is positioned centrally. Natural light streams through the large windows, illuminating the wooden beams and walls, while a stone fireplace adds to the warmth of the room.

Vacation home in Holmes

5 out of 5 average rating, 23 reviews

The Dahlia Villa within Westerhall Gardens

Reconnect with nature at this unforgettable escape. A gorgeous mature garden in a park like setting. Two queen bedrooms, great room, 75 inch TV. Radiant bathroom floor. Outdoor 45,000 gallon salt pool…that’s shared with other property (summer months - POOL IS FOR REGISTERED GUESTS ONLY - NO EXCEPTIONS) Decompress in our sauna. This a no smoking/vaping property. A sprawling 17plus acre estate. Dahlia Villa is a beautiful two bedroom completely independent unit on the estate.

Superhost

An indoor heated pool reflects sunlight through large windows, offering views of snow-covered slopes and trees. The serene water glimmers, while the ski trails are visible in the distance, framing a relaxing atmosphere.

Vacation home in Dover

4.83 out of 5 average rating, 35 reviews

Walk to Mount Snow, Cozy, Clean and Comfortable

You can walk, drive or take the shuttle to the slopes. Our unit has some views of the mountain. We strive to give you a fresh, clean, and comfortable condo for that memorable winter getaways. On top of being so close to Mount Snow, you have a garden-level unit with a private deck, a fireplace with complimentary firewood, and a warm heated pool. Our condo will comfortably sleep up to 4 guests, and a full-size kitchen with all the pots and pans for you to cook a special meal.

Guest favorite

An inviting pool area is shown, featuring a clear blue water surface reflecting the sunlight. Lush green mountains rise in the background, while a well-maintained terrace surrounds the pool. Seating is available nearby, contributing to a relaxing outdoor environment.

Vacation home in Hancock

4.96 out of 5 average rating, 24 reviews

Ski in/Ski Out - Building 1 Condo at Jiminy Peak

Book today and spend your ski days only steps from the lift! Get first tracks or even night ski from this one bedroom condo in Building 1 at The Country Inn at Jiminy Peak. Private parking, kitchenette, and all of the comforts of home. Visit any season to explore this beautiful Berkshire mountain. Enjoy private, gated parking, walk to the country store to get essentials, and even rent equipment right at the mountain. A family-friendly condo with food options for all.

Guest favorite

An outdoor hot tub is positioned adjacent to a wooden deck with steps leading up to a cozy house. A picnic table sits on the gravel area below the deck, surrounded by lush greenery and trees.

Vacation home in Tannersville

4.95 out of 5 average rating, 20 reviews

Mountain escape in Hunter/Tannersville

Nestled between Hunter and Tannersville, our cozy house is 5 minutes from Hunter Mountain and hiking trails. Enjoy skiing, snowboarding, hiking, lakes, zip-lining, and more. Nearby are great restaurants, boutique stores, theaters, a supermarket, and more. Our home has four spacious bedrooms, two bathrooms, a full kitchen, and a living area for entertaining. Enjoy ping-pong, the outdoor hot tub, or gather around the fire pit for a mountain bonfire!

Guest favorite

A serene view of the Narrow River reflects the blue sky and surrounding greenery. A wooden dock is visible on the right, leading to the water's edge, while trees provide a natural border along the bank.

Vacation home in South Kingstown

5 out of 5 average rating, 25 reviews

Beautifully furnished 3 bedroom vacation house!

Beautifully furnished, sun-drenched home! You will love our updated home steps away from the Narrow River. It is under 10 minutes from the beaches and 15 minutes from Newport! New finishes, furniture, and central air throughout. Enjoy cooking and entertaining in the open-concept kitchen with state-of-the-art granite and gas oven range. Large backyard with patio and grille. Great house for families, couples, and friends.

Top guest favorite

A sunlit seating area is surrounded by large windows, providing views of nature outside. A suspended hanging chair is complemented by two woven armchairs. A round coffee table rests on a textured rug, creating a cozy gathering space with a warm wood ceiling and floors.

Vacation home in Broadalbin

4.99 out of 5 average rating, 113 reviews

Great Sacandaga Lake | 15-min to Saratoga Springs

In search of a unique getaway? The Lodge at Glampful is the heart of your ADK adventure. Fishing Kayaking Hiking Skiing | Snowshoeing | Sledding 44Lakes Craft Beverage Trail Retreat on a semi-private 50-acre property - surrounded by rolling meadows, hiking trails, a spring-fed creek, and more! Royal Mountain: 29-min Saratoga Springs: 29-min Lapland Lake: 30-min Lake George: 45-min Plan your getaway today!

Guest favorite

A private entrance is approached by a pathway lined with gravel and natural stones, leading to a wooden deck. The home features a modern grey exterior, complemented by a lush green lawn and a large tree, providing a serene and tranquil setting.

Vacation home in Great Barrington

4.95 out of 5 average rating, 215 reviews

Home in Great Barrington. Steps from downtown!

Central and Private! Just steps away from historic downtown Great Barrington and East Mountain Hiking trails. Enjoy sunset views with friends and family, before you walk into town for a night out! 10 minutes (2 miles) to Butternut Ski Area This brand new home features all new appliances and furniture. Enjoy luxury, charm, and privacy while you rest easy at The Maple.