Vacation home rentals in Western Massachusetts

Find and book unique vacation home rentals on Airbnb

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Popular amenities for Western Massachusetts vacation home rentals

Family-friendly vacation home rentals

A scenic view is presented from the deck, showcasing a vibrant landscape of green trees and expansive mountains under a clear blue sky. Natural light enhances the tranquility of the outdoor space.
Vacation home in Cairo
4.65 out of 5 average rating, 23 reviews

Chalet on the Hill

StephanieRating, 5 stars46 months ago
We had a lovely stay at Chalet on a Hill and Nadine was lovely to work with. House is very private with great views and close drive to Windham where dinner was recommended. The grocery store nearby has everything you need if you want to make the house feel like home for the weekend. We will certainly look to book again.
Superhost
Vacation home in Ludlow
4.75 out of 5 average rating, 84 reviews

Ludlow Big Family Fun Home

DerekRating, 5 stars1 month ago
Kelly was super responsive. The house was 5 minutes away from Okemo.
Guest favorite
A fenced backyard is visible, featuring a grassy area with a decorative lantern hanging from a tree. Two chairs are placed on the lawn, and a stone path leads towards the rear of the property, where a raised deck is positioned.
Vacation home in Hudson
4.9 out of 5 average rating, 120 reviews

2 blocks to Warren ST w/ a yard and parking

DennisRating, 5 stars3 weeks ago
Excellent location, close to all the art galleries, cafes and restaurants Hudson has to offer. It is also a short drive to other points of interest like Olana, the Thomas Cole house and Catskill, NY.
Superhost
A bright sunroom features a cozy seating area with colorful throw pillows and a patterned blanket over a spacious daybed. Large windows allow ample natural light, while a plant adds a touch of greenery. The welcoming space includes a simple area rug and access to the outdoors.
Vacation home in Hudson
4.85 out of 5 average rating, 128 reviews

Great top fl near cnter with sunroom and a view cc

AmandaRating, 5 stars3 weeks ago
The space was clean, cozy, and exactly as advertised! We had no trouble getting in, and Vladimir was very responsive and flexible about our check-in time. We were easily able to walk to the center of town and to the Amtrak station, and all of the best restaurants in Hudson are nearby.
Superhost
Vacation home in Hudson
4.79 out of 5 average rating, 85 reviews

2 blocks to Warren ST with an office and a yard cb

StefanRating, 5 stars5 months ago
Booked the place for a guest visiting. They loved the place. Was clean and spacious. Would rent again.

Vacation home rentals with a patio

Guest favorite
A spacious great room is highlighted by large windows that provide views of the surrounding greenery. A cozy seating area features a plush sofa and armchair, situated on a vibrant area rug. Rustic wooden beams and a ceiling fan add warmth to the inviting open space.
Vacation home in Mount Holly
4.98 out of 5 average rating, 40 reviews

Okemo Oasis - 6 Bedrooms, 3.5 Baths, 2 Kitchens

DavidRating, 5 stars1 month ago
The Okemo Oasis home was a fantastic place for our annual cousins’ ski trip. It had plenty of space for everyone to sleep, relax, and enjoy the open living, dining, and kitchen area. The many bathrooms was a big plus, and check-in was seamless. There were very few downsides—the beds weren’t the most comfortable but were manageable for a short stay, and the road access was a bit tricky, though that’s beyond the host’s control. While there was no cellular service, they had WiFi. Overall, it’s a great home, and we would definitely stay here again!
Guest favorite
A shared backyard is depicted with a well-maintained grassy area and garden beds. Stone pathways lead through the space, which features a seating area and a fire pit. Surrounding wooden fencing provides privacy, while the backdrop includes a small shed and nearby vegetation.
Vacation home in Hudson
4.96 out of 5 average rating, 28 reviews

La Maison Hudson: Charming 1BR In Prime Location

Melissa And TimRating, 5 stars1 month ago
We absolutely loved our stay! It was so close to town, but very peaceful and quiet at night. The home had everything we could need, and was a perfect spot to relax in between exploring Hudson. Highly recommended!
Guest favorite
Vacation home in Wappingers Falls
4.96 out of 5 average rating, 51 reviews

Once in a Lifetime Hudson River Views

JeffRating, 5 stars2 months ago
A true retreat spot- peaceful with lots to do. The home is a perfect Air BnB- lots of bedrooms, great hang out spaces, fun amenities (pool table, ping pong, hot tub, huge tv), awesome kitchen. The topper is the amazing river setting! One of the best spots I have stayed. Highly recommend!
Top guest favorite
Vacation home in Gardiner
5 out of 5 average rating, 30 reviews

Country oasis on 75 acres with pond and hiking

ZsofiaRating, 5 stars4 months ago
A beautifully remodeled country home in an amazing location; with a view of Shwangunk Mountains and the Hudson valley, surrounded by large open fields, providing privacy and perfect for stargazing. The home is spacious, comfortable, tastefully furnished, perfect for a party of 6 to even 8 people. The kitchen has all the best equipments, tools. The "on demand" hot water system worked very well for us. Shane is a wonderful host, very responsive and helpful. There are amazing hiking trails close-by or one can just walk around the area and enjoy the outdoors right on the property. We very much hope to come back sometimes in the spring or summer time for some hiking and enjoying what this wonderful home provides with visitors.
Top guest favorite
Vacation home in Glens Falls
4.98 out of 5 average rating, 57 reviews

Cozy home near Lake George & Saratoga

VincentRating, 5 stars1 month ago
GREAT HOUSE, GREAT SERVICE.... HOPEFULLY WILL BE BACK
Superhost
Vacation home in Salt Point
4.92 out of 5 average rating, 65 reviews

Riverfront, cozy farmhouse near Rhinebeck

ShariRating, 5 stars3 weeks ago
The house is so well preserved yet the updates make it feel comfortable and modern. The fireplace was awesome to share with our family on a cold and rainy night. Being close to the waterfall/river was also lovely. We were there between seasons, and in the summer it must be divine.
Guest favorite
Aerial view of a spacious house surrounded by trees, featuring a heated pool with four chaise lounges positioned nearby. A barbecue area and outdoor seating are visible on the deck, alongside a small shed. Solar panels are installed on the rooftop.
Vacation home in Kingston
4.93 out of 5 average rating, 67 reviews

Secluded hilltop getaway | heated pool + hot tub

AllieRating, 5 stars2 months ago
This is our third time staying at Mark and Anne’s house and we are already looking forward to coming back! Mark and Anne are INCREDIBLY responsive and very helpful. This is the perfect place for a get to gather with friends or family. The house is stunning and has everything you need - perfectly private location as well! Thank you Mark & Anne!
Superhost
The spacious living area features a large gray sectional sofa and a flat-screen television. An expansive window offers a view of greenery outside, while natural light brightens the room. A wooden dining table is positioned nearby, enhancing the room's functionality.
Vacation home in Woodbury
4.85 out of 5 average rating, 20 reviews

UNIQUE and GORGEOUS historic loft style rental

AdamRating, 5 stars1 week ago
Jamie is a fantastic host! She is also kind-hearted and very hospitable. For example, Jamie asked me to let her know if I would be arriving after dark during check-in in order to leave the lights on for me and she checked in with me during this longer stay to see how everything was going, offering me recommendations for restaurants in the area or nearby hiking spots. If you get the opportunity to stay at her beautiful home I highly recommend it! Thank you Jamie!

Vacation home rentals with a washer and dryer

Guest favorite
A wooden railing frames a peaceful view from the deck, showcasing a diverse landscape of trees and open fields. The sky displays varying shades of grey and blue, hinting at a tranquil atmosphere. The changing foliage suggests the transition of seasons.
Vacation home in East Durham
4.94 out of 5 average rating, 49 reviews

Beautiful 2 bedroom home with panoramic view

ChristopherRating, 5 stars5 months ago
I have stayed at this home many times and it never disappoints . All ways very clean and check in and out very easy . I would definitely recommend this home .
Superhost
A charming cabin exterior features a light yellow facade with white trim and a gray door. Two large windows flank the entrance, allowing natural light to illuminate the interior. Surrounding greenery adds a natural touch to the tranquil setting.
Vacation home in Temple
4.83 out of 5 average rating, 52 reviews

Cozy Cabin in a Rural Setting #16

MarciaRating, 5 stars1 month ago
The cabin was clean, cosy & comfortable and a good location to have my pets.
Superhost
A wooden dock extends over calm water, reflecting the surrounding trees and sky. Lush greenery frames the scene, with a few clouds visible above. The tranquil atmosphere of the lake invites relaxation and a connection to nature.
Vacation home in Becket
4.96 out of 5 average rating, 51 reviews

Perfect Serene Waterfront All Season Retreat!

RachelRating, 5 stars2 months ago
Quiet neighborhood. House and property are welcoming and just as described. We had a snowstorm check-in day and Larry was responsive and made sure the snow and ice were cleared prior to our arrival. The kids and the dog enjoyed exploring the property despite the single digit temps and 20 inch base of snow. This property is close to so many awesome winter activities! We made the most of our 4 night/5 day stay and went cross country skiing at Canterbury Farm, snow tubing at Bousquet Mountain, and snowboarding at Otis Ridge. It was great to have a well appointed kitchen for home cooked meals, and a woodstove with plenty of firewood to beat the frigid temps. Overall - awesome!
Superhost
A bright bathroom is featured, with light blue walls and two framed floral prints hanging for decoration. A white sink stands against the wall, complemented by a turquoise bath mat on the wooden floor, while soft natural light filters in through a window.
Vacation home in Pittsfield
4.83 out of 5 average rating, 23 reviews

Explore the Berkshires from this charming home.

NickRating, 5 stars2 months ago
Lovely place, exactly what my family needed
Vacation home in Athens
4.88 out of 5 average rating, 100 reviews

Lakefront Retreat | Kayaks, Paddle Board & Hot tub

SalRating, 5 stars1 month ago
Great space, beautiful lake, host was friendly and responsive, no problem getting an uber to Athens and Hudson. Would absolutely stay here again.
Top guest favorite
A spacious outdoor area is surrounded by trees, featuring a fire pit with seating arranged in a circle. A mix of bright turquoise and neutral chairs are positioned around the stone fire pit, while a tennis court is visible in the background, set within a grassy landscape.
Vacation home in Windham
4.93 out of 5 average rating, 15 reviews

Perfect Windham getaway for year round fun!

RitaRating, 5 stars8 months ago
Some essentials in place such as toiletries coffee salt etc Home was comfortable and suitable to meet our needs Would definitely return
Top guest favorite
The bathroom features a modern glass shower with a rainfall showerhead and marble walls. A wooden vanity with a smooth countertop supports a round sink, complemented by stylish light fixtures above the mirror. Natural light from an adjacent window adds brightness to the space.
Vacation home in Dover
5 out of 5 average rating, 44 reviews

Large elegant 2BR in Village walk to restaurants!

JenniferRating, 5 stars3 days ago
Big thank you to Rich & Nicky, their place was gorgeous, spacious and comfortable for my parents, sister and our dogs. We felt right at home. They were very responsive and helpful throughout the weekend, a pleasure to communicate with. House was a 5 min drive to Carinthia, 9min drive to Wilmington. We took their recommendation and had my 40th birthday/easter brunch at the Sawmill just across the street, delicious. Went to the Alpenglow Bistro the night before for dinner, we couldn’t be more pleased with the dining options this stay. Was happy to have skied this late in April in southern, VT as well! Would highly recommend staying at the 1827 House when visiting Mount Snow and the surrounding area. High end features like the towel drying racks were an added bonus and the espresso machine was a hit! Will definitely be booking again!
Guest favorite
Vacation home in Sunapee
5 out of 5 average rating, 38 reviews

Sunapee Barn Retreat

CarolRating, 5 stars4 months ago
Entertainers paradise! Kitchen was fully stocked with platters, glasses, place settings, and specialty baking and cooking equipment. Just bring the food and nothing else is needed. Enough space for a kids and adult party on separate floors. Decorate well in minimalist style with all the modern conveniences. Even though there was a surprise snow storm on a holiday, was kept in the loop with plowing. They were very attentive. Thank you! Made many memories.

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