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 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, 143 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, 174 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 Pine Hill

4.98 out of 5 average rating, 133 reviews

The Perfect Catskills Escape for Families and Groups

Pine Hill House is a renovated 1870s boarding house with loads of old charm mixed in with new luxuries. Take a left from the house to find miles of hiking trails. Take a right and walk to town with its vibrant restaurant scene and a lively community center. Belleayre Beach and Belleayre ski area are both a 5-minute drive away, as are some of the Catskills' hottest restaurants, spas, and cider houses. Don't want to leave? Relax around the woodburning stove and soak in the clawfoot tub.

Guest favourite

Holiday home in Shandaken

4.97 out of 5 average rating, 142 reviews

Unique BellEayre River retreat

#2024-STR-AO-85 As seen in Chronogram magazine Chronogram/docs/chronogram-april-2023 High ceilings, Rough cut beams, All new HVAC and Hearthstone soapstone wood burning stove. 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". Dogs welcome (Up to 2), sorry no cats.

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.

Guest favourite

Holiday home in Derry

4.97 out of 5 average rating, 120 reviews

Little Lake House- ice skating, getaways & more

Welcome to our home away from home. This cozy lake get away just minutes over the border from Massachusetts is the perfect place to connect with friends and family. Enjoy days out on the water which is right outside your back door! Or nights at the fire pit enjoying the stars. We have wifi, tv w/ streaming services, laundry, a/c & heat, and kayaks to make your stay as comfortable and fun as possible. We're family friendly and have a crib for infant/baby.

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.

Guest favourite

Holiday home in Beacon

5 out of 5 average rating, 60 reviews

Private, modern carriage house. Great for couples.

Newly built in 2022, our charming, modern carriage house is tucked away within a small courtyard garden on a quiet residential street in the heart of Beacon NY. Guests will enjoy an efficient, elegantly designed and furnished interior with views of the Mount Beacon ridgeline from this comfy and private abode. The owners are long-time Airbnb hosts who work hard to ensure their guests have a peaceful, relaxing stay.

Guest favourite

Holiday home in Great Barrington

4.95 out of 5 average rating, 189 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.