
Cottage vacation 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

Waterfront cottage overhanging the water!
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!

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!
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.

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

Ye Little Wood | Cozy Forest Cottage with Hot Tub
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.

Hot Tub - Walk to the Beach - Mins to Mtns - Lakes
Great little spot for a getaway!

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!

Hot Tub & Chic Catskills Woodstock Design Retreat
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

Be in Nature at this Gorgeous Riverfront Cabin
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.

Cozy Vermont Antique Sugar House with Fireplace
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.

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!

Magnolia Cottage
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!

Newly Built Cottage in Housatonic Valley
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!

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.

Beautiful stream side cottage in the woods
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!

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.
Private cottage rentals

Old Mill Cottage - Upstate Mountain Views
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.

Intimate Cottage on Private Estate
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.

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!

Cozy Cottage on Cedar Lake- "Cottage Cheeze"
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.

Cozy, Quiet Cottage on Country rd 2 mil from I-91
Perfect place to get away for some peace and quiet. Very clean. So comfortable I didn’t even leave to explore the area!
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- Six Flags New England
- Bushnell Park
- Taconic State Park
- Jiminy Peak Mountain Resort
- Albany Center Gallery
- Berkshire East Mountain Resort
- Bash Bish Falls State Park
- Catamount Mountain Ski Resort
- Kent Falls State Park
- Mount Greylock Ski Club
- Brimfield State Forest
- Mount Snow Ski Resort
- Norman Rockwell Museum
- Beartown State Forest
- Dinosaur State Park
- Mohawk Mountain Ski Area
- Hartford Golf Club
- Bright Nights at Forest Park
- Bigelow Hollow State Park
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Naumkeag
- Pineridge Cross Country Ski Area
- Clarksburg State Park