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 Albany

4.97 out of 5 average rating, 115 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.

11–18 Jan

₹14,781 per night

Guest favourite

Holiday home in Winchester

5.0 out of 5 average rating, 9 reviews

Lakefront Elegance with your own private beach

The Lake Level of this home is all yours. This leads to a swimmable sandy beach and peaceful kayaking lake or just sunbath on the beach. This space has 1000 sq ft of space with a private full bathroom. The town has two family restaurants within two miles of the home. Both Brattleboro Vt (15 min) and Keene NH (10 min and a college town) are larger towns with multiple choices to eat out and pubs to choose from. Pisgah Park or Gardner Mt for hiking trails. No smoking, guests, pets or cooking.

13–20 Jan

₹19,048 per night

Guest favourite

Holiday home in Warren

4.99 out of 5 average rating, 113 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

3–10 Aug

₹29,393 per night

Guest favourite

Holiday home in Torrington

4.96 out of 5 average rating, 135 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.

17–24 Nov

₹12,839 per night

Guest favourite

Holiday home in Hancock

5.0 out of 5 average rating, 8 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.

27 Nov – 4 Dec

₹12,875 per night

Guest favourite

Holiday home in Hudson

4.95 out of 5 average rating, 112 reviews

Private Hudson Retreat w/ Hot Tub + Fireplace

Escape to Falls Road – a private mid-century home nestled at the edge of 20 acres of preserved woodlands. Our home has been thoughtfully updated, featuring an array of resort quality amenities as well as a wood-burning fireplace, soaking tub, outdoor shower, projector & a 4ft deep cedar hot tub to unwind in. The yard includes a deck, propane grill, and fire pit. Located just over 2 hours from NYC/Boston and only 8 miles from Hudson center. Minutes to hiking, golf, & more!

7–14 May

₹27,735 per night

Guest favourite

Holiday home in Town of Rockingham

4.96 out of 5 average rating, 53 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.

27 Sep – 4 Oct

₹12,952 per night

Superhost

Holiday home in Becket

4.95 out of 5 average rating, 42 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!

3–10 Dec

₹22,157 per night

Guest favourite

Holiday home in Shandaken

4.98 out of 5 average rating, 97 reviews

Unique BellEayre River retreat

#2024-STR-AO-85 As seen in Chronogram magazine Chronogram/docs/chronogram-april-2023 High ceilings, Roughcut beams, All new HVAC and primitive fire heat. Take it easy at this tranquil getaway while you see and hear only the water flow with wrap around 4 season river right off porch. Close to scenic hiking, skiing, river tubing, and great restaurants along "Rapid Water"- The Algonquin Nation word for "Shandaken". you won't be disappointed.

24 Sep – 1 Oct

₹15,916 per night

Guest favourite

Holiday home in Williamstown

4.97 out of 5 average rating, 70 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.

30 Aug – 6 Sep

₹15,126 per night

Guest favourite

Holiday home in Hawley

5.0 out of 5 average rating, 48 reviews

Retro 1970s home in the Berkshires

Contemporary home with a dramatic interior set on 50 beautiful acres in the secluded countryside of the Berkshire foothills. This home was initially designed and built for a notable children's book author in the 1970s and features his personal studio within it's multi-level bright and modern interior. Outside, decks wrap around the house with views of the gardens and access to nearby recreation.

8–15 Jun

₹35,244 per night

Guest favourite

Holiday home in Coxsackie

4.97 out of 5 average rating, 180 reviews

Waterfront w/Dock, Kayaks, Fishing

Warm and welcoming - with views that rival a Thomas Cole painting. Heron's View is one of the best spots on the Hudson River. Just a 5 minute walk to the new Wire Event Center, along with shops, restaurants, park, playground and pavilion in the Historic District of Downtown Coxsackie. Superb hiking, golf, and breweries nearby, 15 mins to Catskill, NY, 20 mins to Hudson, NY, 30 mins to skiing.

30 Nov – 7 Dec

₹50,007 per night