
Chalet vacation rentals in Western Massachusetts
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Top-rated chalet rentals in Western Massachusetts
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Popular amenities for Western Massachusetts chalet rentals
Family-friendly chalet rentals

The King's Cottage
Had an amazing time her with my friends. Very clean place and super nice cabin in the woods. Make sure you have a 4wd drive car in the winter to get up the driveway.

Daydream Mountain Art-Chateau | Hot Tub & Pool
This was our second year staying here with friends, and we had such a lovely time. There's plenty to do inside the house itself even on a dreary day, with curiosities and art abound, instruments, games, fireplace, etc, a great kitchen for group meals, and spacious and comfortable rooms otherwise. Olia is very kind and responsive, with plenty tips for the local area. We'd recommend for groups or families in an instant. Nothing like relaxing in the hot tub while looking out at the mountain vista with rain pattering on the porch roof above - pure bliss.

Rustic Sunny Vermont Home near Mount Snow
Couldn't say enough great things about both the hosts and the property. Just lovely home - very spacious, and clean and cosy. The area is gorgeous, with a lot to do. Mt. Snow and Hermitage skiing are very close, and Wilmington and the area are charming. Host was very gracious and kind..thank you!

Cozy Art Chalet | Hot Tub, Ski & Hike Escape
An awesome place for a ski getaway! The house is beautiful, and just down the road from the mountain. Would highly recommend!

Private Catskills Home w. Hot Tub, near Ski Mnt
Great place that was clean, comfortable and cozy. There were excellent instructions for everything and my family loved the hot tub!

Chalet 7min to Ski Stratton-WoodStove,Views,DogsOK
The quiet retreat in Vermont, just like we wanted. We are already comfortable with country living, so being here was easy and peaceful.

Secluded home by Hunter Mountain
Had a lovely time! It’s a beautiful house and Juris sent very clear and helpful instructions before check in. Would stay again.

2BDR- Cozy Windham/Hunter Escape
Such a great and cozy stay! Minutes from town center and Windham, so easy to check in / check out. Very happy we stayed here!
Luxury chalet rentals

Modern Mountain Chalet on 15 Acre Catskills Estate
Lovely stay with family and friends. The host went out of his way to ensure our arrival was smooth, even with a very icy driveway and up to two inches of snow falling. The space is beautiful, secluded and serene. But also close to restaurants in Mt. Tremper and good hikes.

Charming Chalet w. Hot Tub - 1 Mile to Mt. Snow
A beautiful spot perched amongst the trees and snowy woods. Cosy couches and fireplaces, a magical hot tub and generous touches, like extra wood, coffee and shampoo. I took my boys skiing nearby and we all loved every minute. Wouldn't hesitate to stay again

New! Custom Chalet minutes from Mt Snow w/ Hottub
The house was fantastic. Great condition, cool layout! There was a ton of snow, and the property was well plowed, shoveled and sanded!

Mount Snow Chalet w/ Ski-Home Trail & Indoor Sauna
The house was super close to the mountain The house had everything you could possibly need in the kitchen Three living rooms which was nice we were unable to turn the sauna on sadly Perfect ski house entrance with a lot of room the take everything off without tracking into the rest of the house Large table to eat and play games on I would definitely stay here again

Secluded Woodstock Retreat with Pool and Sauna
My wife and I stayed at Ron’s place for five nights for a winter getaway. We had a great stay, highlights include a comfortable king bed, a quiet setting, a cozy fireplace, and the large ground floor bathroom that feels like your own spa- we thoroughly enjoyed the sauna, huge bathtub, and rain shower. Ron was a great host and was very responsive with any questions we had. We spent many hours watching TV on the screen and projector set up, we grabbed more pillows from upstairs to add some more cushion to the leather couch downstairs.

Luxe HOT TUB, SAUNA 8–12 min Stratton & Mount Snow
So hyggelig! Hygge House is 100% what it promises. Wonderful, peaceful place to escape the busy life for a few days and relax in a beautiful house in a beautiful forest. Hot tub, sauna, cosy house, surrounded by nature. Near all activities of Stratton area. We even got five inches of new snow making it winter wonderland in April.

Modern Zen Chalet at the Foot of Gunks w Mt. View
Spent two nights at this lovely property. For me it's perfect, spacious and remote but still in a great location. You're close to everything, have a beautiful home and outdoor space to enjoy, and Serg/Aaron are extremely helpful with anything you might need. Highly recommend and loved my stay 👍

Beautiful Windham Ski/Summer House
The house was spacious, clean, beautiful and private. We loved the view of Windham Mt from the second floor! The fireplace, expansive but cozy couch and downstairs game room were a hit! Half of my family skied and half stayed at the house to relax. Being 5 minutes from the mountain was fantastic and the house was perfect. Great restaurants nearby, where we had lunch, but the rest of the time we cooked in. Well equipped open kitchen! Hope to be back many times!
Lakefront chalet rentals

Direct Waterfront A-Frame, Close to 3 Ski Areas!
What a great lake house! My family and I went up with the dogs and had such a great time. The place was child friendly, dog friendly, the host was responsive, the hot tub was relaxing, and the view was beautiful. Although we went up when the weather was still too cold to go swimming, the hot tub made for a relaxing evening. This place had everything we were looking for. Thank you

THE LAKEFRONT CHALET - SKI, RIDE, GOLF, BIKE, HIKE
This place was perfect for our Mom’s Book Club Retreat. The living room was spacious enough for all 7 of us but still so cozy for chatting and reading (we were looking at tags to buy the same couches). The weather was terrible so we didn’t get to enjoy the outdoor spaces as much as we’d like but the hot tub and fire pit were great. The kitchen had everything we needed to cook all our meals . Communication and check in were a breeze. Would definitely recommend this place!

Waterfront lakehouse in Berkshires
The chalet was perfect for our relaxing 5 day vacation. We enjoyed swimming off the dock and taking the kayaks out on the lake. The space is wonderful and the view is amazing! We found it hard to get motivated to go out to dinner and lunch because we didn't want to miss one second of the wonderful view!

Large & Sunny Lakefront Home-kayaks/fire pit/games
This was such a relaxing home to spend a celebratory weekend in! We had a great time at Adnan's home over the weekend. The setting is so peaceful, right on the water and we enjoyed the fire pit one evening. The space is large, with plenty of room for all. The house is a little bit dated, but with that said, it had everything we needed for a lake-weekend! On top of that, Adnan could not have been more accommodating and responsive.

Waterfront Lake Home, close to Hunter & Windham
Lovely and relaxing stay. Easy to find and very clean. We loved using the kayaks too!

Chalet Sonsie: A Sweetwater Stay
My family and I booked this place for a relaxing weekend to unplug and we got just that! The kitchen had everything we needed, the couches were extremely comfortable, and the view was great! We would love to come back again soon.

Lake Sunapee Get Away
Carl was a great host and extremely responsive. He helped make the check in/out process extremely easy and was extremely responsive with any questions. There was snow shovels and salt to deal with snow which was helpful. He helped navigate an issue right away and was very generous with offering help even though he was somewhat unavailable. The house was a great location and very clean, and could accommodate a large group easily. The open floor plan for the kitchen/dining room/living room was very nice and we enjoyed the new range for cooking. Carl even helped to make sure we forgot something that we left at the house after contacting us that it was there! Overall, I would highly recommend staying here.

Maple Lodge - Luxury Cabin
This place is amazing and top notch! The perfect house in the perfect location, with a wonderful host - TJ outdid himself! TJs house is spotless with so much room for families/large groups, and the views are breathtaking. The fire-pit, kids play area - every detail was thought of and we couldn’t appreciate it more. Drinking my morning coffee on the master balcony while looking at the lake, I can’t wait to come back! We are already planning our next stay here. I would highly recommend anyone to stay here! Thanks TJ!
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- Jiminy Peak Mountain Resort
- Catamount Mountain Ski Resort
- Albany Center Gallery
- Berkshire East Mountain Resort
- Six Flags New England
- Taconic State Park
- Mohawk Mountain Ski Area
- Bushnell Park
- Mount Sugarloaf State Reservation
- Mount Greylock Ski Club
- Hartford Golf Club
- Kent Falls State Park
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- Mount Snow Ski Resort
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- Otis Ridge
- Norman Rockwell Museum
- Naumkeag
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- Bigelow Hollow State Park
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- Rockledge Golf Club
- WIckham Park
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