Cottage vacation rentals in Western Massachusetts

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Popular amenities for Western Massachusetts cottage rentals

Cottage rentals with a hot tub

Superhost
Cottage in Ledyard
4.88 out of 5 average rating, 207 reviews

Waterfront cottage overhanging the water!

JenRating, 5 stars4 weeks ago
We thoroughly enjoyed our time at the cottage. It was so very peaceful and we loved being literally right around n the water! Slept amazingly well and the cottage was just lovely! Robert was also a great host. 5 stars all around and we hope to return again!
Top guest favorite
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 favorite
Cottage in Saratoga Springs
4.98 out of 5 average rating, 120 reviews

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

Mairéad ElizabethRating, 5 stars1 day ago
Our three-night stay at the cottage was great! Amanda quickly responded to any questions or concerns I had. The cottage had a fully stocked kitchen and the outside grill worked great. The backyard was not huge but lots of fun nonetheless with different lawn games, furniture, hammock and hot tub. It was sweet in the evening with the torches lit and tree lights on. Everything was very clean and well-maintained. The beds and linens were divine; soft sheets and very comfortable mattress. Overall a great place to stay. We enjoyed nearby Victoria pool and Saratoga Spa State Park.
Superhost
Cottage in Litchfield
4.86 out of 5 average rating, 348 reviews

Litchfield-Hot Tub-Shops & Eats-Vineyards-Hikes

Mary EllenRating, 5 stars6 days ago
Martin's cottage in Litchfield was a little piece of heaven!! My sister and I stayed for 4 days. The first 2 days we had to work remotely and were delighted to 'set up shop' in the adorable dining room with a large sliding glass door looking out on the beautiful back yard - internet connection was flawless and we were able to totally focus in the blissful quiet of the rural location. After attending the funeral of our dear aunt in Southington, we had some time to explore Litchfield's adorable shops and fine restaurants. We both slept so soundly each night in the wonderful beds and left 're-charged' and 'de-stressed' after our stay!! I feel that I've found a treasure and a true getaway, even if just for a long weekend. Super-easy to get to Bradley airport and the route is so scenic! The Fall would be an IDEAL time to come to this cottage. Finally, Martin was, indeed, a super-host, as rated in Airbnb!! Extremely responsive and kind, each time I reached out to him!
Top guest favorite
Cottage in Kerhonkson
4.99 out of 5 average rating, 174 reviews

Ye Little Wood | Cozy Forest Cottage with Hot Tub

EmmaRating, 5 stars3 weeks ago
Danny and Travis are excellent hosts ! The house is gorgeous and extremely clean and well maintained. The kitchen is very well stocked with cooking utensils/ pots which is awesome for people who enjoy cooking (like we do). This is our second time staying here and we absolutely love it and plan to return.
Superhost
Cottage in Gilmanton
4.85 out of 5 average rating, 102 reviews

Hot Tub - Walk to the Beach - Mins to Mtns - Lakes

JessicaRating, 5 stars3 weeks ago
Great little spot for a getaway!
Superhost
Cottage in Red Hook
4.9 out of 5 average rating, 206 reviews

LAKE COTTAGE WITH HOT TUB - PAINTED TURTLE

JenniferRating, 5 stars1 month 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 favorite
Cottage in Boiceville
4.98 out of 5 average rating, 114 reviews

Hot Tub & Chic Catskills Woodstock Design Retreat

JordanRating, 5 stars4 months ago
We always stay at Little Willow when we go skiing at Belle Ayre. I think our three years and running relationship with the house tell you all you need to know about working with the Little and Littler gang and their spot.

Pet-friendly cottage rentals

Guest favorite
Cottage in Poughkeepsie
4.91 out of 5 average rating, 356 reviews

Be in Nature at this Gorgeous Riverfront Cabin

AaryaRating, 5 stars1 week ago
We loved the place, it was a beautiful home with lots of light and accessible green space. It was perfect for a short getaway. It’s a short drive from nearby towns and was very easy to find based on the directions. Mark was a responsive and accommodating host and we had a wonderful time in his airbnb.
Top guest favorite
Cottage in Newfane
4.99 out of 5 average rating, 235 reviews

Cozy Vermont Antique Sugar House with Fireplace

AlanRating, 5 starstoday
I really appreciated the warm welcome from Dennis and Lenore, they made us feel right at home. They had helpful recommendation for local dining after they provided a full tour and history of the premises. A truly unique, comfortable and historic property with a very comfortable bed. (and my son loved the cinnamon swirl muffins !). Will definitely plan to stay again.
Guest favorite
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!
Top guest favorite
Cottage in Boiceville
4.99 out of 5 average rating, 122 reviews

Magnolia Cottage

JenniferRating, 5 stars2 days ago
We really enjoyed our stay here! The space was clean and cozy. The location was quiet, but also conveniently located within walking-distance to a great bakery and a craft beer/snack store. Highly recommend this stay!
Guest favorite
Cottage in Cornwall
4.92 out of 5 average rating, 157 reviews

Newly Built Cottage in Housatonic Valley

KimRating, 5 stars6 days ago
I came to this area to hike the Appalachian Trail, and this place was just perfect for me. Lucy’s place is spotless, with tons of bright light and two great spots to sit outside and enjoy the nature. I loved that there was a French press available, and the bed was super soft, as well as the pillows. I also really liked the cozy squishy couch. The TV had streaming services, which was great for when I was working. I also spoke to a few neighbors who were passing by, and they were really friendly. They were kind enough to give me some suggestions for things to see in the area. I’m looking forward to visiting again!
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 favorite
Cottage in Kerhonkson
4.88 out of 5 average rating, 227 reviews

Beautiful stream side cottage in the woods

HallieRating, 5 stars4 weeks ago
The perfect private and secluded cottage engulfed in beautiful trees and sat besides a natural stream. My weekend was a great refresh and relaxing experience with my partner! Around a 35 minute drive to Woodstock and Kingston, with tons of closer local places to explore as well. Loved the decor and vibe of this cottage!
Top guest favorite
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.

Private cottage rentals

Guest favorite
Cottage in Clintondale
4.97 out of 5 average rating, 315 reviews

Old Mill Cottage - Upstate Mountain Views

MonicaRating, 5 stars3 days ago
I’m so glad we stayed there! We had a beautiful breakfast on the deck one day and looked at all the stars at night. Perfect place.
Guest favorite
Cottage in Rhinebeck
4.92 out of 5 average rating, 154 reviews

Intimate Cottage on Private Estate

SelinaRating, 5 stars3 weeks ago
Lovely cottage and a perfect location if you’ll be at Omega Institute which is 4 minutes away. Close to Rhinebeck Village too. Beautiful grounds and well appointed home. Extremely clean and well planned space. Comfortable bed, soft linens. Spacious kitchen made meal prep easy and when I asked about a blender the host was very responsive and a new blender was waiting for me on the porch. Really restful place with a private and calming back porch. Very serene property. I cooked dinner instead of going out on Saturday night because the space is so welcoming and relaxing, especially after a long day of classes at Omega. Comfortable sofa, wool throw, and Netflix. A perfect evening. Would love to stay again the next time I’m in the area.
Top guest favorite
Cottage in Newfane
4.97 out of 5 average rating, 130 reviews

Silk Purse Cottage on Baker Brook

KathyRating, 5 stars2 days 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 favorite
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 favorite
Cottage in Vernon
4.97 out of 5 average rating, 113 reviews

Vintage Bolton Lake

JohnnyRating, 5 stars2 days ago
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 favorite
Cottage in Saugerties
5 out of 5 average rating, 387 reviews

Carriage House on Falls, Walk to Village

VincentRating, 5 stars1 week 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!
Guest favorite
Cottage in Sturbridge
4.91 out of 5 average rating, 153 reviews

Cozy Cottage on Cedar Lake- "Cottage Cheeze"

DougRating, 5 stars1 week ago
Mary Elle's cottage was the perfect mid week getaway. We found it clean and very cozy. Spent hours on the spacious deck enjoying the views on Cedar Lake. Paved driveway provided off road parking and easy access for unpacking and reloading our luggage. Already thinking about a return visit.
Guest favorite
Cottage in Bernardston
4.88 out of 5 average rating, 326 reviews

Cozy, Quiet Cottage on Country rd 2 mil from I-91

AmyRating, 5 stars6 days ago
Perfect place to get away for some peace and quiet. Very clean. So comfortable I didn’t even leave to explore the area!

Destinations to explore