Cottage holiday rentals in Western Massachusetts

Find and book unique cottages on Airbnb

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Popular amenities for Western Massachusetts cottage rentals

Cottage rentals with a hot tub

Top Guest favourite
Cottage in Burlington
4.98 out of 5 average rating, 120 reviews

Cozy Lakefront Cottage w/Swim Spa & Firepit

PatrickRating, 5 stars2 weeks ago
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!
Guest favourite
Cottage in Saratoga Springs
4.97 out of 5 average rating, 119 reviews

The King's Cottage- HOT TUB and Pet Friendly!

ScottRating, 5 stars2 days ago
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.
Top Guest favourite
Cottage in Plymouth
5 out of 5 average rating, 21 reviews

Lakefront Getaway | Hot Tub | Game Room | Fire Pit

RamonRating, 5 stars1 week ago
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%!
Guest favourite
Cottage in Bloomington
4.96 out of 5 average rating, 234 reviews

Couples Getaway, Hot Tub, 3 acres, 5mi to Kingston

NoaRating, 5 stars1 month ago
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.
Guest favourite
Cottage in Saugerties
4.89 out of 5 average rating, 186 reviews

Hits Adjacent | Pet Friendly | Caraway Cottage

LucyRating, 5 stars1 week ago
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!
Top Guest favourite
Cottage in Pownal
4.98 out of 5 average rating, 42 reviews

Beautiful, 100 Acre Retreat, Williamstown 10 Mins

AlbertRating, 5 stars2 days ago
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.
Superhost
Cottage in Red Hook
4.9 out of 5 average rating, 206 reviews

LAKE COTTAGE WITH HOT TUB - PAINTED TURTLE

JenniferRating, 5 stars4 weeks ago
Thank you Ellen for the easeful stay at your cottage with clear instructions. The surroundings are beautiful. We saw an eagle at the lake!
Guest favourite
Cottage in Bethlehem
4.98 out of 5 average rating, 107 reviews

Cozy Getaway | Pet Friendly | Litchfield Cty

AmyRating, 5 stars1 week ago
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

Guest favourite
Cottage in Craryville
4.92 out of 5 average rating, 535 reviews

Columbia County Getaway - Raspberry Ridge Cottage

May AnnRating, 5 stars4 days ago
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.
Guest favourite
Cottage in Catskill
4.97 out of 5 average rating, 109 reviews

Evergreen Escape - Woodsy Artistic Retreat

AllenRating, 5 stars3 weeks ago
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!
Superhost
Cottage in Rhinebeck
4.93 out of 5 average rating, 289 reviews

Ridgetop 2 Br Cabin- Views, 130acre forest & falls

EliasRating, 5 stars2 weeks ago
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.
Guest favourite
Cottage in Jamaica
4.83 out of 5 average rating, 529 reviews

Cottage 7min to Ski Stratton-WoodStove,Views,DogOK

EmmaRating, 5 stars3 days ago
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!
Top Guest favourite
Cottage in Port Ewen
4.99 out of 5 average rating, 159 reviews

Swan Cottage with Expansive Hudson River Views

JayneRating, 5 stars1 month ago
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.
Top Guest favourite
Cottage in Thompson
4.99 out of 5 average rating, 142 reviews

Waterfront Cottage in Thompson CT • Dogs Welcome

HeatherRating, 5 stars5 days ago
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!!
Guest favourite
Cottage in Lanesborough
4.84 out of 5 average rating, 279 reviews

Wildlife Lakeside Cottage; views/wildlife

SonyaRating, 5 stars1 month ago
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.
Guest favourite
Cottage in Sheffield
4.94 out of 5 average rating, 155 reviews

Cheerful 3-bedroom cottage with woodstove.

AvivRating, 5 stars3 weeks ago
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

Superhost
Cottage in Putney
4.82 out of 5 average rating, 271 reviews

The Cottage, a house built for guests.

LeslieRating, 5 stars4 weeks ago
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.
Top Guest favourite
Cottage in Valatie
4.99 out of 5 average rating, 143 reviews

Kinderhook Lakefront Retreat-private, kayaks, ac

DuncanRating, 5 stars2 weeks ago
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.
Top Guest favourite
Cottage in Newfane
4.97 out of 5 average rating, 130 reviews

Silk Purse Cottage on Baker Brook

KathyRating, 5 stars1 day ago
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!
Top Guest favourite
Cottage in Rhinebeck
4.99 out of 5 average rating, 153 reviews

Fabulous Lemon Cottage in Rhinebeck, NY

LizRating, 5 stars2 weeks ago
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!!
Top Guest favourite
Cottage in Vernon
4.97 out of 5 average rating, 113 reviews

Vintage Bolton Lake

JohnnyRating, 5 starstoday
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!
Top Guest favourite
Cottage in Saugerties
5 out of 5 average rating, 387 reviews

Carriage House on Falls, Walk to Village

VincentRating, 5 stars6 days ago
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!
Superhost
Cottage in Highland
4.9 out of 5 average rating, 627 reviews

Little Yellow Cottage New Paltz - Kitchen wash/dry

HardyRating, 5 stars2 weeks ago
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!!
Guest favourite
Cottage in Woodstock
4.95 out of 5 average rating, 425 reviews

Woodstock Mountain Cottage

NicholasRating, 5 stars1 month ago
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!

Destinations to explore