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

4.94 out of 5 average rating, 153 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.

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Holiday home in Gilford

4.81 out of 5 average rating, 129 reviews

4-Season Condo in the Heart of the Lakes Region!

Be in the center of it all! Cozy up in this adorable, modern condo in the heart of the Lakes Region. Stay in and watch movies by the fireplace or enjoy outdoor recreation during all four seasons! Walk across the street to the private beach on Lake Winnipesaukee or enjoy the outdoor pool right in front of the condo! Sit on your private deck w your morning espresso & a peek-a-boo view of Gunstock Mountain! Better yet- there's a walking path from the condo directly to the Bank of NH Pavilion!

Guest favourite

Holiday home in Warren

4.98 out of 5 average rating, 154 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 Broadalbin

4.99 out of 5 average rating, 110 reviews

Discover Saratoga | Sled, Ski, & Soak in Hot Tub

Saratoga Chowderfest: SAT, FEB. 8 11AM - 4PM Restaurants serving samples for $2. 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: 30-min Saratoga Springs: 30-min Lapland Lake: 37-min Lake George: 57-min Plan your getaway today!

Guest favourite

Holiday home in Torrington

4.95 out of 5 average rating, 186 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

4.99 out of 5 average rating, 134 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, 157 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 deck. 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 Derry

4.97 out of 5 average rating, 131 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 Great Barrington

4.95 out of 5 average rating, 202 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.

Guest favourite

Holiday home in Gilford

4.94 out of 5 average rating, 221 reviews

Marty'sBay-RetroCondo, Private Beach, Concert Path

Enjoy a wonderful experience filled with hospitable touches at this centrally located, 1-bedroom condo with private beach access to Lake Winnipesaukee and a direct walking path to the Bank of NH Pavilion. Our unit has a kitchen, private deck, queen bed, sleeper sofa, and lots of amenities. Great for bike week, concerts, trips to the lake, skiing, and hiking trails!

Guest favourite

Holiday home in Coxsackie

4.97 out of 5 average rating, 211 reviews

Peaceful Hudson Riverfront in downtown Coxsackie

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.

Guest favourite

Holiday home in Hudson

4.89 out of 5 average rating, 113 reviews

2 blocks to Warren ST w/ a yard and parking

First floor apartment with backyard and parking Apartment amenities include: Fast internet and WiFi throughout the house Desk and chair for work if needed Iron, hairdryer, and a compact ironing board Appliances: fridge, stove, microwave, range, and coffee maker