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 modern keypad door lock is positioned next to a glass paneled door, allowing for keyless entry. A soft glow from the light outside is visible through the glass, creating a welcoming ambiance. A decorative bow made of burlap and checkered fabric hangs next to the door.

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.

Superhost

Vacation home in Monroe

4.95 out of 5 average rating, 42 reviews

Family Home in the mountains. Get out and explore!

Old-fashioned charm awaits at our comfortable, well-equipped base for your next family adventure. Attractions from art galleries to zip-lining are a short drive away - including hiking, mountain biking, white water rafting, and fly fishing. Mass MoCA, the Clark Institute, Berkshire East, and Mount Snow are nearby. At night, adults can linger over dinner while the kids watch a movie - out of the way - upstairs! We can't wait to welcome your families to share an authentic rustic experience.

Top guest favorite

A modern kitchen sink is situated beneath a wide window, showcasing a snowy outdoor scene. Counter appliances, including a blender and toaster, are visible alongside cleaning supplies. A decorative pot with a small plant adds a touch of green, while a wall clock enhances the space.

Vacation home in Warren

4.98 out of 5 average rating, 166 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, 210 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 private wooden patio features three foldable chairs arranged for relaxed seating. The space is surrounded by a wooden railing, offering views of greenery beyond. The weathered wooden deck shows signs of nature with scattered leaves.

Vacation home in Hudson

4.85 out of 5 average rating, 130 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

A snow-covered building stands prominently against a backdrop of a frosty mountain slope. Softly shaped snow drapes over the surrounding trees, while the mountain, lightly dusted with white snow, is visible in the distance under a clear blue sky.

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.

Superhost

Two black lounge chairs are set on a lush green lawn beside a peaceful stream. Two canoes in teal are stored on a wooden platform, surrounded by vibrant greenery and trees. Sunlight filters through the leaves, creating a serene outdoor setting.

Vacation home in Becket

4.96 out of 5 average rating, 52 reviews

Perfect Serene Waterfront All Season Retreat!

Enjoy everything the Berkshires has to offer from this beautiful, secluded, nicely renovated waterfront house set on two wooded acres of forested land. Explore the stream that runs through the property, or just sit on the large deck or down by the crystal clear lake and listen to the sounds of nature while feeling the warm sun on your face. Very private--just one near neighbor. The sunny house has 2 bedrooms, study with sofa bed, 2 full baths, full kitchen!

Top guest favorite

A wooden porch features two Adirondack chairs and a small footrest, all in a rich brown hue. Natural light filters through the nearby windows, illuminating the wooden flooring and the inviting setting. A storage box is positioned beside the chairs.

Vacation home in Williamstown

4.98 out of 5 average rating, 96 reviews

ALL welcome: Lovely 1 BR studio, Berkshires beauty

Come as you are - we welcome ALL visitors. Relax and soak in your surroundings in this new 1 bedroom vacation spot. Part of a barn conversion, the space is clean and bright and ideally located for those exploring all the Berkshires has to offer. Perfect for an individual or couple looking to escape to a serene and beautiful setting - a stream abuts the property and hiking/snowshoeing trails are accessible out the front door.

Top guest favorite

A sweeping aerial view captures a snow-covered mountain landscape, with ski trails marked by distinct lines on the slope. A cluster of homes and roads are visible at the base, surrounded by pristine white terrain and dense evergreen forests under a clear blue sky.

Vacation home in Dover

5 out of 5 average rating, 45 reviews

Large elegant 2BR in Village walk to restaurants!

This is the first-floor unit at the historic 1827 House where you can escape to beautiful VT!! Enjoy the spacious great room, full kitchen, & laundry. AC for the Summer! Vermont Adventure Challenge starts next door! Close to everything in the Village. Walk on sidewalks to fine restaurants, pubs, wine tasting, weddings, antiques, escape rooms, Free Moover shuttle & trails right from the house. A very unique stay!!

Top guest favorite

A spacious lodge with an inviting orange facade is presented among lush green grass. Large windows allow for ample natural light, while a prominent deck extends from the upper level. Surrounding trees and a well-maintained lawn enhance the serene outdoor setting.

Vacation home in Broadalbin

4.99 out of 5 average rating, 115 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!

Superhost

Vacation home in Pittsfield

4.83 out of 5 average rating, 23 reviews

Explore the Berkshires from this charming home.

The whole group will enjoy easy access to everything from this centrally located place. Ski Bousquet, Butternut, or Jiminy Peak. Visit charming towns of Great Barrington, Lee, Stockbridge, Lenox, Adams, N. Adams and Williamsburg. All within a short drive. Soak up some culture by visiting Clark Museum, Mass Moca, or the Rockwell Museum, or listen to some great live music at Tanglewood during the summers.

Superhost

The private entry features a dark door with an arched window, framed by white curtains that softly billow in the breeze. A small seating area is visible to the side, with a decorative metal stove positioned nearby, creating an inviting outdoor space.

Vacation home in Woodbury

4.86 out of 5 average rating, 22 reviews

UNIQUE and GORGEOUS historic loft style rental

Beautifully bright third floor loft style space with private entry available for your enjoyment. Basic kitchen, laundry, and bath are located on the second floor. Due to the stairs in this unique space, it would be ideal for a single traveler or couple looking for a getaway. Walkable to historic Woodbury, minutes to amazing land trust hiking trails in Roxbury, and only 1.5 hours from NY City.