Holiday Homes in Western Massachusetts

Find and book unique holiday homes on Airbnb

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Popular amenities for Western Massachusetts holiday homes

Family-Friendly holiday homes

Superhost
Holiday home in Hudson
4.81 out of 5 average rating, 107 reviews

3 block to Warren ST with a Yard and parking ga

EmilyRating, 5 stars6 months ago
My friends & I loved being so close to Warren Street! We were able to walk to all the shops and restaurants. It was so nice not having to drive anywhere.
Holiday home in Cairo
4.65 out of 5 average rating, 23 reviews

Chalet on the Hill

StephanieRating, 5 stars48 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
Holiday home in Ludlow
4.75 out of 5 average rating, 84 reviews

Ludlow Big Family Fun Home

DerekRating, 5 stars3 months ago
Kelly was super responsive. The house was 5 minutes away from Okemo.
Guest favourite
Holiday home in Hudson
4.9 out of 5 average rating, 125 reviews

2 blocks to Warren ST w/ a yard and parking

ErinRating, 5 stars2 weeks ago
We had a great time staying at this Airbnb. It was clean, spacious and close to Warren St. Communication was clear and it was easy for us to get into the apartment. We also appreciated being able to check in early. Thank you!
Superhost
Holiday home in Hudson
4.91 out of 5 average rating, 100 reviews

2BRT 3 blocks to Warren ST

SiddhantRating, 5 stars7 months ago
A really great place with clear instructions and wonderful flexibility from the host. Has everything you could need and is very cozy too.
Superhost
Holiday home in Hudson
4.86 out of 5 average rating, 133 reviews

Great top fl near cnter with sunroom and a view cc

BethanyRating, 5 stars2 weeks ago
We had a great stay, and the place is exactly as advertised. It was clean, beds were comfortable, and it was proximate to town. Only downside was the noise from being on a main road, but the window units helped drown out the noise.
Superhost
Holiday 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 stars7 months ago
Booked the place for a guest visiting. They loved the place. Was clean and spacious. Would rent again.

Holiday home rentals with a patio

Guest favourite
Holiday home in Hudson
4.97 out of 5 average rating, 35 reviews

La Maison Hudson: Charming 1BR In Prime Location

ColleenRating, 5 stars2 weeks ago
Cybele's home was the perfect weekend getaway! Walking distance to the best restaurants, cafes, shops--but on a quiet street that felt like a perfect retreat! Will stay here next time I'm in Hudson.
Guest favourite
Holiday home in Wappingers Falls
4.96 out of 5 average rating, 52 reviews

Once in a Lifetime Hudson River Views

CarolineRating, 5 stars3 months ago
Wonderful home and beautiful surroundings. Jean was very responsive.
Top Guest favourite
Holiday home in Glens Falls
4.98 out of 5 average rating, 61 reviews

Cozy Glens Falls home near Lake George & Saratoga

AlexRating, 5 stars2 weeks ago
I loved the coziness of the home The accommodations The Neigbors Much better than staying at a hotel for sure Little more costly But surly worth it It rained all day, one day there And it was nice being stuck in doors all day We’re in a hotel You would have been Let’s go to a movie or something We got to get out of this small space Just all around the place added a great addition to my awesome trip Thank you I would diffently stay there again
Holiday home in Salem
4.65 out of 5 average rating, 75 reviews

Chez Moo - Hot Tub with a View

MelindaRating, 5 stars5 days ago
This was the second time we have stayed here and we were pleasantly surprised at the cleanliness and the way the house looked upon arrival. We had everything we needed and made ourselves at home. The hot tub was not maintained but with the help of our chemist and engineer we were able to use it. We hope we will be able to come again. Thanks Melinda Risse Nutter
Guest favourite
Holiday home in Highland
5 out of 5 average rating, 32 reviews

Charming Vacation House w/ Pool & HotTub

ConstanceRating, 5 stars3 weeks ago
Beautiful place. Comfortable beds. Quiet neighborhood. Michele was communicative. Really enjoyed my memorial day weekend.
Guest favourite
Holiday home in Saratoga Springs
4.89 out of 5 average rating, 27 reviews

Beautiful 4bedroom home overlooking Saratoga lake.

JamesRating, 5 stars6 months ago
We were looking for a place to host thanksgiving dinner for 7 near my in-laws. Sandra's home near Lake Saratoga worked perfectly. Very large, open concept and huge kitchen with long dining table was exactly what we needed. With 4 bedrooms and 3 baths, it meant staying there was easy with space for us all. The on.y challenge for us was the steep driveway as we got hit with snow and rain. I would highly recommend this Airbnb.
Guest favourite
Holiday home in Lake George
4.94 out of 5 average rating, 63 reviews

The Loft - Discount Rates ‼️ Lake George.

AbigailRating, 5 stars1 month ago
This is a very cozy home for a peaceful getaway. All the furniture was so comfortable. We got the best nights sleep in the bed. We appreciated the style in decor and how easy it was to find everything we needed. The home was filled with quality items and the personal touches made our stay special. This was our first time visiting the Lake George area and we fell in love with it. Look forward to returning.
Guest favourite
Holiday home in Kingston
4.93 out of 5 average rating, 71 reviews

Secluded hilltop getaway | heated pool + hot tub

AdarRating, 5 stars3 weeks ago
We had an amazing time! The house and its surroundings are spacious, beautiful, and peaceful. The kitchen is fully equipped, making it super fun and easy to cook for a big group. Mark was so kind and responsive, helping us out with everything we needed right away.

Holiday home rentals with a washing machine and dryer

Holiday home in Hancock
4.8 out of 5 average rating, 5 reviews

Winterberry Lodge: Newly Renovated at Jiminy Peak

NicoleRating, 5 stars8 months ago
We had a lovely stay in MA. We weren’t in the Airbnb much but the time that we did spend was quiet and peaceful. Blown away by the communication and responsiveness of the host. I left an earring behind and the host reached out to me a day after we checked out, and mailed it to me immediately. Super grateful for such a helpful host and a wonderful experience in the mountains!!
Superhost
Holiday home in Temple
4.83 out of 5 average rating, 52 reviews

Cozy Cabin in a Rural Setting #16

MarciaRating, 5 stars2 months ago
The cabin was clean, cosy & comfortable and a good location to have my pets.
Guest favourite
Holiday home in Chesterfield
5 out of 5 average rating, 20 reviews

Spofford lake 1 bedroom apartment with boat dock

JackRating, 5 stars22 months ago
Scott was a terrific host and his place was exactly as we expected. Large and spacious, very comfortable bed. We had a few rainy days and were stuck inside a bit more than we expected, but Scott’s place was warm and comfortable, and we didn’t feel crowded in. Would stay there again.
Top Guest favourite
Holiday home in Sandisfield
5 out of 5 average rating, 13 reviews

Berkshires Modern Cabin with Babbling Brook

JeanneRating, 5 stars20 months ago
We enjoyed our stay at Deborah’s place. It was as advertised. The kitchen was well stocked. We used the gas grill. The babling brook sounded lovely. We walked from the cabin and were able to see good fall color. Particularly enjoyed the wood burning stove, great on cool evenings.
Holiday home in Athens
4.88 out of 5 average rating, 100 reviews

Lakefront Retreat | Kayaks, Paddle Board & Hot tub

SalRating, 5 stars3 months 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 favourite
Holiday home in Athens
5 out of 5 average rating, 22 reviews

Peaceful 3-Bed/3-Bath in Private Lake Community

LauraRating, 5 stars3 weeks ago
James and Alison have a beautiful, well equipped home. It’s large enough for a family of eight and has everything you want and more in a home away from home. They’re welcoming and very responsive. I recommend their place highly and hope to return for a longer stay. You can’t go wrong staying here.
Guest favourite
Holiday home in Dover
5 out of 5 average rating, 11 reviews

Kingswood 4 BR 4 Bath House

HeatherRating, 5 stars3 months ago
This home was great for an extended family ski weekend. The home was very comfortable, clean and very nicely decorated. It was perfect for relaxing after a day on the slopes. The Moover shuttle is very convenient and picks up right in front of the house to go to the base of Mount Snow. We would definitely return again.
Holiday home in Hartford
4.53 out of 5 average rating, 32 reviews

Lux Boutique Large Private LOFT Pratt St Hartford

KarolinaRating, 5 stars1 month ago
place was spotless. a little noisy during quiet hours but to be expected on a saturday night. would stay again.

Destinations to explore