
Holiday Homes in Western Massachusetts
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Top-rated Holiday Homes in Western Massachusetts
Guests agree: These holiday homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for Western Massachusetts holiday homes
Family-Friendly holiday homes

3 block to Warren ST with a Yard and parking ga
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.

Chalet on the Hill
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.

Ludlow Big Family Fun Home
Kelly was super responsive. The house was 5 minutes away from Okemo.

2 blocks to Warren ST w/ a yard and parking
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!

2BRT 3 blocks to Warren ST
A really great place with clear instructions and wonderful flexibility from the host. Has everything you could need and is very cozy too.

Great top fl near cnter with sunroom and a view cc
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.

2 blocks to Warren ST with an office and a yard cb
Booked the place for a guest visiting. They loved the place. Was clean and spacious. Would rent again.
Holiday home rentals with a patio

La Maison Hudson: Charming 1BR In Prime Location
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.

Once in a Lifetime Hudson River Views
Wonderful home and beautiful surroundings. Jean was very responsive.

Cozy Glens Falls home near Lake George & Saratoga
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

Chez Moo - Hot Tub with a View
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

Charming Vacation House w/ Pool & HotTub
Beautiful place. Comfortable beds. Quiet neighborhood. Michele was communicative. Really enjoyed my memorial day weekend.

Beautiful 4bedroom home overlooking Saratoga lake.
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.

The Loft - Discount Rates ‼️ Lake George.
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.

Secluded hilltop getaway | heated pool + hot tub
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

Winterberry Lodge: Newly Renovated at Jiminy Peak
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!!

Cozy Cabin in a Rural Setting #16
The cabin was clean, cosy & comfortable and a good location to have my pets.

Spofford lake 1 bedroom apartment with boat dock
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.

Berkshires Modern Cabin with Babbling Brook
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.

Lakefront Retreat | Kayaks, Paddle Board & Hot tub
Great space, beautiful lake, host was friendly and responsive, no problem getting an uber to Athens and Hudson. Would absolutely stay here again.

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

Kingswood 4 BR 4 Bath House
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.

Lux Boutique Large Private LOFT Pratt St Hartford
place was spotless. a little noisy during quiet hours but to be expected on a saturday night. would stay again.
Destinations to explore
- Hudson Valley Holiday rentals
- Boston Holiday rentals
- The Hamptons Holiday rentals
- Long Island Holiday rentals
- Plainview Holiday rentals
- East River Holiday rentals
- New York Holiday rentals
- Pocono Mountains Holiday rentals
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- Cottage rentals Western Massachusetts
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- Rentals with pools Western Massachusetts
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- Six Flags New England
- Albany Center Gallery
- Bushnell Park
- Jiminy Peak Mountain Resort
- Taconic State Park
- Berkshire East Mountain Resort
- Catamount Mountain Ski Resort
- Kent Falls State Park
- Bash Bish Falls State Park
- Mount Greylock Ski Club
- Mount Snow Ski Resort
- Brimfield State Forest
- Norman Rockwell Museum
- Dinosaur State Park
- Mohawk Mountain Ski Area
- Beartown State Forest
- Hartford Golf Club
- Bigelow Hollow State Park
- Bright Nights at Forest Park
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Naumkeag
- Brignole Vineyards
- Bousquet Mountain Ski Area
- Things to do Western Massachusetts
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