
Condo holiday rentals in The Berkshires
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Top-rated condo rentals in The Berkshires
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Popular amenities for The Berkshires condo rentals
Weekly condo rentals

One bedroom condo at Mountain Creek Resort
We really enjoyed our stay! The condo was VERY clean, full stocked with all of the needed essentials and in a great location right by the ski slope. Both the bed and pull-out coach were SUPER comfortable. All instructions were super clear, and the recommendations were perfect. Thank you for letting us stay at your place, we love Mountain Creek!

Cozy Updated 2 Bedroom Corner Condo
Greg has to be the most responsive, accommodating host I've ever had the pleasure of renting from. He gave me clear instructions, responded the minute I sent a question, and was very generous regarding check in and check out. What a great guy! The condo itself is in a great location. We didn't use the Moover but the stop is right outside the building's door. Like many ski condos it's basic but cozy. The neighbors were really audible in the bedroom, but we may have just had a weekend with some loud people next door! The best part (besides how great Greg was) is the view. It's so lovely to look out over the ski mountain. Overall a great value and a wonderful host. Thanks, Greg!

'Bear Paw Lodge' w/Hot Tub* at BASE of Mt Snow
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.

Windham-Hunter Lodge
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.

Ski in/out - 2BR Condo - Indoor Pool/Spa
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.

Studio 3 BEDS-SLEEP 4
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.

Seasons on Mount Snow | Walk Out / Ski Home!
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.

Courtyard Overlook @ Spa Owners Residential Condo
Lovely experience, easy to navigate due to clear instructions from Joe. Although I was there for one night, the area offers a lot of experiences, highly recommend it
Pet-friendly condo rentals

Pet Friendly Stratton West
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

Cozy Condo by Fairfield U/SHU | Patio | Wshr/Dryr
This was our second stay at Dariel’s place. It is perfect for our family and I always check to see if it is available when we are visiting the area. It is spacious yet cozy, and well-appointed. It is easy to get to, and central to both sides of town.

Great 2 bedroom condo at Stratton Mountain
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!!

Stratton Mountain vacation spot
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 & walking distance to cafés *spring avails*
Cozy apartment, walking distance from the water front. Had a great weekend getaway.

Cozy, Pet friendly Luxe condo w/Mountain Views
Had a wonderful repeat stay. The living room is especially lovely on a sunny day with tremendous natural light flooding in. We enjoyed sitting and reading and playing board games there after a morning on the mountains. We really felt at home and will be sure to stay again if we return to the area!

2 Bedroom + Parking Cozy Condo•Mountain Creek•
Great communication and easy checkin, spotless & stylish! We had a wonderful last minute spring getaway from the city. Compared to other airbnbs around, seemed comparatively good value for money. We cooked meals in the apartment and the kitchen is well appointed for doing so; there is also a keurig and French press.

The Oasis of Vernon
We really enjoyed the stay hope we could stay longer. Alejandra is super nice and responsive. It's located in a beautiful community. Room is very clean and has everything you need.
Condo rentals with a pool

Mountain View Townhome w/ Community Pool!
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!

CASiNO, Spa, Hot Tub, Pool, Private Villa, Kingbed
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.

Mt Snow Ski In/Out at Seasons
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.

5-Star Lux Condo: Ski-In/Out, Heated Pool, Hot Tub
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!

Peaceful Oasis steps from Mohegan Sun
We loved our time at Christina’s villa! I mentioned to her that it was a mini honeymoon getaway and Christina left us a bottle of wine, chocolates, a nice card and some other snacks! The villa smelled extremely clean and nice upon entry. The extra amenities such as toothbrushes, and everything else you might have forgotten was a great added touch! We will definitely be back for another stay and will be recommending to others as well!

The Vacay Villa
Krista place is very clean and welcoming. It had perfect personal touches. From coffee creamer for our morning coffee, to shower essentials. I find the small personal touches so nice and it is welcoming. Christa offered east check in and extended my check out time with no questions ask. This was a very nice place for a weekend trip and we will def be booking again!

✰ 255 Mountain Creek Luxury 1 bd Deluxe sleeps 5
Great communication and accurate description of the condo. Everything worked (codes, tv, internet ect.) and was in good shape.

Stratton Duplex Condo Steps to Lifts, Village!
Great walkable location. Loft space granted nice privacy for 2 couples or extended family. Fireplace and living room were cozy.
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