Condo vacation rentals in Western Massachusetts

Christine's place was the perfect home base for hiking and other activities in the area. It's cozy, well-located, and offers beautiful views from a screened-in porch that's right on the water. I'd happily stay here again!

My family of four had plenty of space for a relaxing weekend. Weather did not permit skiing but Mt Snow was right next door and Okemo ~60 mins away. Nice amenities in a great location.

Cullen was an exceptional host. The space was exactly as described, with plenty of supplies. Communication was stellar. The condo had plenty of extras like clean linens and blankets, there were even additional chargers set up and toiletries if we needed. The beds are comfortable. The bathrooms very clean and updated. Parking right in front. We felt safe and comfortable. This AirBnB is 5 minutes to Windham mountain and minutes from Town. Plenty of places to eat and shop. I highly recommend this Host and property. If we ever go back, we will try to re-book with Cullen.

Great condo at Mt Snow. Very clean and organized. Location is on the mountain. It requires some steep walking for ski in/ski out so keep in mind for younger kids while also carrying their gear. My kids are older so it wasn’t an issue for us but worth mentioning. Eric is the perfect host - always reachable and responsive. Super accommodating when he’s able to be. We got unlucky wind hold weather and he offered to extend our check out if we wanted to ski an extra day to make up for it. Truly awesome. Can’t go wrong.

I highly recommend Suzanne's place for anyone visiting Windham! She was incredibly responsive and helpful throughout the booking process and my stay. As someone who travels constantly for work, my schedule can be quite unpredictable, and Suzanne was unbelievably accommodating and flexible with my changing needs. I truly appreciated her understanding and willingness to work with me. The location is fantastic, right in the heart of Windham, and the view of the ski resort from the back deck was an unexpected bonus! I only wish I could have stayed longer. I'm already looking forward to my next visit, not just for winter skiing, but also to explore the beautiful surroundings throughout the year.

Noah’s unit was absolutely wonderful. I’m not sure if the listing says this but it’s literally in front of a lift! The ski in ski out isnt a short walk. It’s right in front of the doorway. Also I’ve never been so close to a CAT grooming the trails. The unit itself was well stocked, with a great fireplace and spacious three bedrooms. Noah was responsive and very easy to communicate with. And very accommodating esp for a last minute trip! We’d love to return to this place!

It was exactly how described by management and pics. We felt at home and kitchen had everything one needs. Greg the manager was incredibly responsive and professional…. We would go back.

Megan’s place was great for a weekend of skiing at Stratton. Right on a shuttle route that picks you up at the front door and is very reliable. Clean and comfortable. Megan was extremely helpful and responsive throughout the whole process from booking to check in and check out.

Little smaller than what the photo showed. Overall exactly as stated in the description. Location is great and the host is extremely responsive and friendly. One of the better hosts in my experience

Great place to stay conveniently located by the mountain base! We enjoyed walking into the village after skiing. Very clean and cozy and had everything we needed and more. Dana was very responsive! Hope to come again next year!!

Second stay at William’s. Loved it again the second time, great area and super close to Mt Snow resort. Great restaurants and of course the Snow Republic Brewery nearby. Thanks for the great stay!

We had a great stay at this cozy condo, perfectly located on a shuttle route to Stratton Mountain. The convenience of being just minutes from the slopes made our ski trip stress-free.

Cozy apartment, walking distance from the water front. Had a great weekend getaway.

Very close to Mount Snow. Walking distance to market, coffee house and Dover Bar and Grill. A dog friendly rental with everything you need for a ski trip.

We had a great time staying at Kens place! Ken was very responsive and accommodating! Thank you!

Place was perfect! Right on the mountain for easy access to Magic Mountain. The kids loved the game room! Patrick and Erin were easy to communicate with and very responsive. We can’t wait to come back next year!

Elizabeth is a phenomenal host, the place is one of the best I ever stayed in.. super clean, well stocked, (especially the kitchen made great impression) very clean.. An excellent value for the money… big and accommodating…

Anne is an amazing host and this townhouse is fabulous. Perfect for a mountain stay. Comfortable, spacious, great view of the mountain, clean, modern yet cozy. Very convenient to everything in the area. I cannot say enough about it, but having such a great host was the cherry on top, especially since we were there for an extended period!! You cannot go wrong!

Kim’s place was perfect for what me and my daughter needed. We were in the area celebrating her 15th birthday. The villa was clean, and quaint. The decor of the room was peaceful and warm. And most importantly it was CLEAN, no complaints! Kim was responsive and proactive in her communication. Will definitely visit again in the future and recommend to any friends and family who might travel that direction.

The unit is very comfortable for a family and very convenient to Mount Snow. Updated bathrooms and washer/dryer. Great clubhouse and pool facilities at Seasons condo. Andrew was a pleasure to work with.

An excellent place to stay for a ski trip. Perfect location right at the base. Wonderful building with a great pool and hot tub. Excellent for a great ski vacation!

We really enjoyed our stay. The villa was well decorated, clean, and cozy. It had such a relaxing vibe, I wish we had more time there. It was close to the casino and walking distance to the spa. It was great qetaway. The host also went out of the way to add personal touches.

This was a perfect location to stay during the AAU tournament at Mohegan Sun! Very cozy and comfortable space! Everything we needed plus board games and cards that provided laughs and great family time! The host was very friendly, helpful and responsive! Would definitely stay here again!

Camilla's place was beautiful! Perfect for a date night. The amenities were amazing. The condo even had things like toothbrushes, q-tips, make up remover. I felt right at home. Extremely clean and tidy with lovely decor. 10/10! :)