Holiday home rentals in Western Massachusetts

Find and book unique holiday home rentals on Airbnb

Top-rated holiday home rentals in Western Massachusetts

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

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Guest favourite

Holiday home in Broadalbin

4.99 out of 5 average rating, 105 reviews

ADK Getaway: Fall Foliage, HotTub & Hiking Trails

**Ask me how to unlock a free day and enjoy discounts for extended stays!** 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! **Near** Royal Mountain: 30-min Saratoga Springs: 30-min Lapland Lake: 37-min Lake George: 57-min Plan your getaway today!

Guest favourite

Holiday home in East Hampton

5 out of 5 average rating, 42 reviews

Family Friendly Lake House Lake Pocotopaug Sunsets

Enjoy this newly renovated and decorated, cozy retreat on the lake! With breathtaking views and sunsets, this beautiful lakefront cottage provides a peaceful setting that offers an unforgettable experience for anyone visiting. The 3-bedroom, 2-bathroom cottage is full of charm with cozy indoor and outdoor living spaces. Including an outdoor undersea mermaid mural. With all the amenities of a larger home, this cottage on the lake is the perfect place to make memories that will last a lifetime.

Guest favourite

Holiday home in Albany

4.95 out of 5 average rating, 146 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.

Guest favourite

Holiday home in Monroe

4.95 out of 5 average rating, 41 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.

Guest favourite

Holiday home in Warren

4.98 out of 5 average rating, 142 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 favourite

Holiday home in Torrington

4.94 out of 5 average rating, 173 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.

Guest favourite

Holiday home in Hancock

4.94 out of 5 average rating, 18 reviews

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

*NEW to AirBnB* 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

Holiday home in Hudson

4.85 out of 5 average rating, 119 reviews

Great top fl near cnter with sunroom and a view cc

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 favourite

Holiday home in Town of Rockingham

4.96 out of 5 average rating, 75 reviews

Cozy studio at Leslie's Tavern in Rockingham

All new construction and amenities. Quiet patio and beautiful ly landscaped space. Conveniently located at exit # 6 91 we are very easy to find. The studio is situated in a separate space detached off the back of the restaurant with separate entrance and private outdoor patio. Parking is a few feet from your entrance in our parking lot. We are located is 2 miles north of historic Bellows Falls and 25 minutes from Okemo. Leslie your host is on premise all the time.

Superhost

Holiday home in Becket

4.96 out of 5 average rating, 49 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!

Superhost

Holiday home in Salt Point

4.91 out of 5 average rating, 54 reviews

Riverfront, cozy farmhouse near Rhinebeck

This historic Clinton Hollow house was built by Isaac Fraleigh in the late 1700's and overlooks the waterfalls of Wappingers Creek. The house has the architectural details of an antique colonial and the open, spacious feel of a modern contemporary. The great room with its big fireplace has different vibes and seating areas and is just perfect for family and friends gathering. The Petanque field in the garden add a fun convivial activity.

Guest favourite

Holiday home in Williamstown

4.98 out of 5 average rating, 90 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.