
Cottage holiday rentals in Western Massachusetts
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Top-rated cottage rentals in Western Massachusetts
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Popular amenities for Western Massachusetts cottage rentals
Cottage rentals with a hot tub

Cozy Lakefront Cottage w/Swim Spa & Firepit
We had a GREAT time at Feyza’s cabin. It was clean, quiet and exactly as described. We especially loved the secluded setting, the lake views and the jacuzzi. Feyza was helpful, communicative and very responsive. Her digital guidebook was very insightful as to the local attractions and restaurants. We would definitely stay here again!

The King's Cottage- HOT TUB and Pet Friendly!
The cottage was perfect for a weekend trip to Saratoga Springs. It was the perfect location, walkable to the town and SPAC. We also really enjoyed its easy access to the park and its trails. The cottage itself was also great. The furnishings were very comfortable and looked just like the pictures. The back yard and its furnishing were perfect for relaxing after the day. We would definitely stay again during our next trip to the area.

Lakefront Getaway | Hot Tub | Game Room | Fire Pit
Such a lovely home! actually better than I expected! Will definitely book again. It’s honestly a no brainer after staying there. I can recommend this place 100%!

Couples Getaway, Hot Tub, 3 acres, 5mi to Kingston
We had a lovely stay at kim’s. The location was great, having a hot tub was really nice even with the weather getting warmer, the space was very clean and kim was very responsive to us throughout the whole stay.

Hits Adjacent | Pet Friendly | Caraway Cottage
The perfect stay for horse showing at HITS! My only hesitation in writing this review is that I didn't want anyone else to know about this place for future horse shows! ;) An excellent place to stay with above and beyond amenities, easy check in and great for traveling with a dog. Will absolutely be back!

Beautiful, 100 Acre Retreat, Williamstown 10 Mins
An incredibly beautiful, immaculate cottage with lovely mountain views and the most thoughtful, generous, and responsive hosts! Scott and Annika absolutely deserve their title as "Superhosts." We felt like we had our own private resort with a luxurious hot tub and a fire pit under the stars. Scott and Annika sent clear instructions for how to let ourselves into the cottage and had a great online guidebook. A kind handwritten note was there to welcome us. Scott and Annika checked in with us often to ask if we needed anything, and they were quick to respond to any questions we had. They set up the cottage with extra comforts such as slippers and snacks, and we really enjoyed using the espresso machine. We were especially happy that we were able to bring our 30-lb. dog with us, and we loved exploring all of the nature and art in the nearby Berkshires and southern Vermont. We highly recommend this cottage, and we hope to go back to stay there again soon.

LAKE COTTAGE WITH HOT TUB - PAINTED TURTLE
Thank you Ellen for the easeful stay at your cottage with clear instructions. The surroundings are beautiful. We saw an eagle at the lake!

Cozy Getaway | Pet Friendly | Litchfield Cty
I wanted a weekend getaway for my son’s 13th birthday that landed on Friday the 13th, I came across this cabin airbnb and decided to book and give it a try. this location is an hour away from our home and gave us that peace of paradise we were looking for. the cabin felt like home and had everything you can possibly need. I honestly wish I can give higher than a 5 star because this cabin was perfect. I’ll be booking again for a winter weekend getaway. thank you for hosting my family and I.
Pet-friendly cottage rentals

Columbia County Getaway - Raspberry Ridge Cottage
Ilze and Laurence’s place felt like home away from home. Every morning, we were greeted with chirping birds, clucking hens (was even able to order a dozen eggs straight from their free-range poultry—so organic!)—and a smiling donkey! It is a place were you can find peace and rest for your soul even for just a few days.

Evergreen Escape - Woodsy Artistic Retreat
Excellent location for local shopping, lots of food choices, delicious breweries. Most importantly VERY close by for climbing & getting out to nature. The Woodstock & Kaaterskill wilderness areas are within 30 minute drive. Lots of stunning views for a decently low mileage. Rip Van Winkle bridge is 9 minutes away if you want to explore the other side of the Hudson. The place has all the amenities you’d need for a getaway. Very clean, host was very responsive; even on the Memorial Day holiday. Will be back!

Ridgetop 2 Br Cabin- Views, 130acre forest & falls
Rick’s place is great, a nice porch area and two comfortable bedrooms, and the AC is powerful for hot summer evenings. Rick was an excellent communicative host who was at the ready to help out with any issues we had. The only thing, and perhaps I misread something, but I thought it would be more secluded, the 130 acres threw me off. Still, it’s very private and I would recommend this place for your visit to Rhinebeck etc.

Cottage 7min to Ski Stratton-WoodStove,Views,DogOK
Jason’s place was excellent! Exactly what we were looking for in a country getaway-cozy cabin in the woods, full of charm and close to farms, hiking and swimming. we loved listening to the records while cooking. Perfect spot, perfect vacation!

Swan Cottage with Expansive Hudson River Views
Swan Cottage could not have been more perfect for us. We were there for 3 nights and wished it was so many more. Charmingly and beautifully updated and decorated, immaculately clean. Maria thought of everything and was highly responsive. She also had great advice about restaurants, shopping, antiquing, walks, local activities, and more. And the views! The singing backyard birds! We cannot wait to go back. Thank you, Maria.

Waterfront Cottage in Thompson CT • Dogs Welcome
Jane really is a Super host of the cutest cottage ever!! Not only has the cottage exactly as described, it was super clean!! We have never been really comfortable staying at an Airbnb until now!! This cottage and Jane really made our stay one of the best visits to this area we have ever had! We can not recommend this cottage enough! We miss it already and are looking forward to our visit!!

Wildlife Lakeside Cottage; views/wildlife
This is a beautiful and peaceful cottage with easy access to shops and restaurants in the area. It was perfect for a sisters weekend. Highly recommend.

Cheerful 3-bedroom cottage with woodstove.
Just like the pictures , very peaceful and serene , the kitchen is well equipped. The beds are comfy. Great place to relax in the Berkshires. With a super responsive host.
Private cottage rentals

The Cottage, a house built for guests.
This was my second stay at Kathleen’s and it was as comfortable and cozy as the first. This spot is private and peaceful, there’s lots of great outdoors to enjoy nearby, and great local spots for exploring. Would absolutely stay again.

Kinderhook Lakefront Retreat-private, kayaks, ac
Amazing place. Lisa & Steve's cottage made for an amazing weekend. We had pretty bad weather but it was still a great weekend. The lake is so peaceful and the set up of the cottage is perfect. The cottage has everything you need, as well as everything you didnt know you needed! We'll definitely be back. Ate at The Aviary, The Smokehouse & The Maker (Hudson) - all very different but incredible.

Silk Purse Cottage on Baker Brook
The Silk Purse immediately won my heart. From the screened in porch to the big windows and skylight in the bedroom with the sliding door opening out to the little deck, everything featured the music of the brook. I can’t wait to go back!

Fabulous Lemon Cottage in Rhinebeck, NY
By far one of the best airbnbs I have ever stayed at! The cabin was beyond adorable, comfortable, clean, so well decorated and very private. It was so relaxing with great outdoor areas to hang out, places inside to read, comfortable den to watch movies and super comfortable bed. Would definitely come back!!

Vintage Bolton Lake
For seven days, the earth stood still with me in this little cottage on the lake. Listening to the rain falling on the trees, watching the water ripple across the lake and feeling the breeze hit my face on the deck were what I needed to rest for a bit in this quiet oasis. Thank you, Jason, Adam and Xavier, for such a peaceful experience!

Carriage House on Falls, Walk to Village
Great little escape that has you overlooking a waterfall. Very charming interior thats makes it feel incredibly homely, even for its quaint size. The location is a great middle ground for multiple towns, from New Paltz to Woodstock, and Laura and Leo ensure that their guide includes multiple destinations and local restaurant to visit. Great amenities, would definitely choose their property again!

Little Yellow Cottage New Paltz - Kitchen wash/dry
I usually stay in village of New Paltz so was a little apprehensive staying a bit outside of village. But I actually now prefer the situation as it's not that far to all the action and the cottage is amazing, which more than makes up for the minor driving inconvenience. Highly recommend!!

Woodstock Mountain Cottage
This cottage was very lovely, cozy, clean, and just a few minutes from the town of Woodstock, but very secluded and peaceful on a beautiful property. The home was exactly as described and had everything you could need for a short stay. I do recommend having 4-wheel drive and a car with good suspension to get up the gravel road leading to the house. Cayenne is a wonderful host - she was extremely kind and easy to communicate with. I would definitely stay here again!
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- Six Flags New England
- Albany Center Gallery
- Bushnell Park
- Jiminy Peak Mountain Resort
- Taconic State Park
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- Bright Nights at Forest Park
- Hartford Golf Club
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Naumkeag
- Brignole Vineyards
- Bousquet Mountain Ski Area
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