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Compare 25 Cabin Rentals in Winchester with updated reviews, rates, and availability.

Cozy Falls Brook Cabin: Hike & Swim On-Site!

10.0 out of 10, Exceptional, (10)
"The cabin is immaculate and very cute and cozy. It's lovely to be right by the brook in a quiet neighborhood set in a woodsy area. Lots of great places a short right away too. Brattleboro is lots of fun, and we loved hiking in the Manitou Project."
Cozy Falls Brook Cabin: Hike & Swim On-Site!

Cozy Log Cabin on the River | Fireplace | Loft

10.0 out of 10, Exceptional, (7)
"We were looking for a quiet place off season to explore. What a gem. Cabin was very clean and comfy. Hit the weather jackpot with the extended Indian Summer and a few cold nights. Wood stove was great. Nice yard, literally steps to the West River. Views were great in the backyard. If you're a gravel biker, 1/4 mile away from miles of gravel & climbs. Close access to local markets for provisions, beer, beef and other goodies. Host was very responsive answering questions within minutes. ...
Cozy Log Cabin on the River | Fireplace | Loft

Cozy Mount Snow Chalet w/ Game Room & Hot Tub

10.0 out of 10, Exceptional, (8)
"Loved our three night stay. Well located. Wonderful fireplace, easy to use. Hot tub was such a bonus. Comfortable beds. Good communication. Would totally come back!"
Cozy Mount Snow Chalet w/ Game Room & Hot Tub

Cozy Cabin Retreat on Putney Mountain

Cozy Cabin Retreat on Putney Mountain

Jacksonville Cabin w/ Wraparound Deck & Views

9.6 out of 10, Exceptional, (28)
"Perfect cabin with beautiful views."
Jacksonville Cabin w/ Wraparound Deck & Views

Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT

10.0 out of 10, Exceptional, (50)
"Peaceful, beautiful property. Was a relaxing stay, had everything we needed. "
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT

Charming & Cozy River Front Cabin- Close to ski mountains. Ski,Fish,Swim & Hike!

10.0 out of 10, Exceptional, (12)
"Love this property. We had everything we needed and then some. wasn't exactly sure as to where to put the trash as I don't have email on my phone , therefore I didn't receive the email about the trash and laundry until I got back home. I would rather have been able to text but everything worked out for us, and we had a wonderful, relaxing time."
Charming & Cozy River Front Cabin- Close to ski mountains. Ski,Fish,Swim & Hike!

Cozy Log Cabin - Dog Friendly

9.8 out of 10, Exceptional, (9)
"We enjoyed watching movies and games as well as local breweries. The property was very clean, comfortable, and had all the necessities for cooking. We hope to be back one day! "
Cozy Log Cabin - Dog Friendly

Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!

10.0 out of 10, Exceptional, (32)
"We had another great stay for us at the Fiddler's rest. The cabin is beautifully set in a private stetting in the forest. The interior design is colorful and tasteful. The cabin could comfortable host or group of 4 people. The internet connection was great. We would be happy to visit again!"
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!

Mountain Top Escape

9.0 out of 10, Wonderful, (10)
"We love staying at maria’s place. She was very communicative and attentive to our stay there. The location is about 10 minutes from Putney Village, the Putney school, and The Greenwood School. Tons of room and we enjoyed hanging out on the back deck Watching the leaves turn and fall."
Mountain Top Escape

Spacious and comfortable home on a 250 Acre Private Estate

10.0 out of 10, Exceptional, (6)
"The property was wonderful and Joyce the owner was so nice to us. We had a really great week and would go again in a heartbeat!"
Spacious and comfortable home on a 250 Acre Private Estate

Cabin Retreat in Southern Vermont

8.0 out of 10, Very Good, (5)
"Off the beaten path, this cabin offered a cool and quiet respite from the summer heat. Lovely wooded trails to hike, a hot tub to relax in at night, well equipped kitchen and a comfortable bed with a bay window to catch the first morning light. We were traveling with our dog and were pleased to find a place that was pet friendly. We look forward to visiting again"
Cabin Retreat in Southern Vermont

Cozy Updated Log Cabin with Mountain Views close to Monadnock

9.4 out of 10, Exceptional, (20)
"Very nice, clean, and great area. We enjoyed it very much!"
Cozy Updated Log Cabin with Mountain Views close to Monadnock

Alpine A-Frame - midcentury cabin by Lake Raponda

2.0 out of 10, (1)
Alpine A-Frame - midcentury cabin by Lake Raponda

Charming Wilmington Cabin, 8 Mi. to Mt Snow!

9.8 out of 10, Exceptional, (39)
"Perfect cabin if you're looking to decompress and disconnect from every day hectic life. Cute cozy romantic little cabin, owner was on top with communication and accommodations overall an amazing experience."
Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

9.8 out of 10, Exceptional, (8)
"This cabin was so cute and cozy and inside it was all neat! I love the smell of cabins and I love the size of the cabin. It was cold when we got there but that little cabin heats up very well when you turn up the heat. The water takes a couple seconds to warm up, but that's so minimal because the water can get hot. You can adjust the water to stay warm. There's a fridge, a microwave, a TV, dishes, hooks for hanging clothes, trash bins, cleaning supplies, etc... Such a beautiful cabin. It had...
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

Beautiful Lakefront Log Cabin 15 Minutes from Mount Snow

10.0 out of 10, Exceptional, (10)
"Quiet and peaceful lake neighborhood, but convenient to restaurants and shops. Very roomy and comfortable home. Great game room "
Beautiful Lakefront Log Cabin 15 Minutes from Mount Snow

Peaceful Cabin in the Woods and near the mountains

10.0 out of 10, Exceptional, (5)
"This house was amazing. It was so warm and comfortable. The area was quiet and relaxing. It was very clean and the host was super responsive and helpful. Would highly recommend! "
Peaceful Cabin in the Woods and near the mountains

Mount Snow Cabin with Private Hot Tub by RedAwning

3.5 star property
Mount Snow Cabin with Private Hot Tub by RedAwning

Spacious Wilmington Cabin: Walk to Lake

Spacious Wilmington Cabin: Walk to Lake
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Winchester

VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac

10.0 out of 10, Exceptional, (6)
"Everything about this property was beautiful. The home itself being located right on the water was perfect for kayaking, fishing, evenings by the fire, relaxing and reconnecting. The house is gorgeous, comfortable, and had everything you might need/want. We enjoyed the game room - jenga and family air hockey tournaments. A lovely experience and we hope to return at some point. Thank you for sharing your beautiful home with us!"
VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

8.8 out of 10, Excellent, (43)
"Cabin was perfect for our long weekend. Master bed mattress needs an update, but otherwise everything was fantastic."
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

Charming Waterfront Log Cabin

9.6 out of 10, Exceptional, (37)
"We really appreciated the solitude and quiet retreat this cabin offered. "
Charming Waterfront Log Cabin
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.