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Compare 24 Cabin Rentals in Winchester with updated reviews, rates, and availability.

Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna
Room
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna
10.0 out of 10, Exceptional, (1)
"Clean efficient place to stay. A welcome and quiet respite."
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
Vernon Vacation Rental | 1BR | 1BA | 800 Sq Ft | 3 Steps Required
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
10.0 out of 10, Exceptional, (28)
"We had a wonderful time staying at the cabin. Enjoyed the space itself and the property. Quiet, private and peaceful. Looking forward to returning in the winter. "
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
Mountain Views•Summer Sunsets•Private Hiking Tail•Gameroom•Minimalist
Logs, logs and more logs.
Mountain Views•Summer Sunsets•Private Hiking Tail•Gameroom•Minimalist
10.0 out of 10, Exceptional, (26)
"We truly enjoyed our long weekend. The property is well kept and has everything you could need. Relaxing on the porch and taking in the gorgeous view, sitting by the fire at night, and playing in the game room were all highlights!"
Mountain Views•Summer Sunsets•Private Hiking Tail•Gameroom•Minimalist
Mountain Top Escape
Large porch with beautiful views
Mountain Top Escape
9.0 out of 10, Wonderful, (9)
"This place is gorgeous! Really beautiful property, down a long secluded dirt/gravel road. Several friends and family stayed here with me for my sister's wedding. The hummingbirds in particular are just amazing (dozens of them!!). We slept eight folks here, one on the futon and one on a blow up bed. I will say the bedframe in the primary bedroom is a bit squeaky. But overall a lovely place to stay, very nice setup for hosting people for dinner."
Mountain Top Escape
Cozy Updated Log Cabin with Mountain Views close to Monadnock
Property grounds
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
Beautiful Lakefront Log Cabin 15 Minutes from Mount Snow
Summer Vibes on a lake in a quiet Vermont Neighborhood
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
Exterior
Peaceful Cabin in the Woods and near the mountains
10.0 out of 10, Exceptional, (4)
"Spent three nights and everything was great. The house had everything we needed, well equipped kitchen and very comfortable interior. Grounds have a very woodsy feel, loved hearing the owls at night. Easy, very responsive communication with owner."
Peaceful Cabin in the Woods and near the mountains
Personal Wellness Getaway with Included Services, Sauna, and a Private Beach!
Property grounds
Personal Wellness Getaway with Included Services, Sauna, and a Private Beach!
2.0 star property
10.0 out of 10, Exceptional, (1)
"The folks are SUPER and made me feel very welome"
Personal Wellness Getaway with Included Services, Sauna, and a Private Beach!
Jacksonville Cabin w/ Wraparound Deck & Views
Jacksonville Vacation Rental | 3BR | 2BA | 2,000 Sq Ft | Stairs Required
Jacksonville Cabin w/ Wraparound Deck & Views
9.6 out of 10, Exceptional, (26)
"Very nice home on its own road, far from any neighbors, lovely location overlooking pond."
Jacksonville Cabin w/ Wraparound Deck & Views
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
Living area
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
10.0 out of 10, Exceptional, (44)
"Remote, serene and comfortable. No problems."
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!
Interior detail
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 Falls Brook Cabin: Hike & Swim On-Site!
Dummerston Vacation Rental | 2BR | 1BA | 850 Sq Ft | Steps Required
Cozy Falls Brook Cabin: Hike & Swim On-Site!
10.0 out of 10, Exceptional, (7)
"Cabin was perfect for a weekend getaway. Check in was a breeze and they had a very generous check in check out time which I appreciated. It was on a quiet dead-end street so no through traffic and the sound of the brook was calming. The beds were comfortable. It's not that far of a walk from the parking to the house. Happy we could bring our dogs as well. Short drive to town. Love the Vegan Restaurant in Brattleboro the food was delicious. We hiked a few trails that were nearby. Wish we had...
Cozy Falls Brook Cabin: Hike & Swim On-Site!
Rustic Retreat: Cozy Log Cabin
Exterior
Rustic Retreat: Cozy Log Cabin
9.8 out of 10, Exceptional, (8)
"This is a gem in the mountains!! We loves it all, there was more then pitured as well. A picnic table in ba k with the firepit and chaits"
Rustic Retreat: Cozy Log Cabin
Spacious and comfortable home on a 250 Acre Private Estate
Outdoor dining
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
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
Alpine A-Frame - midcentury cabin by Lake Raponda
Welcome to the Alpine A-frame!
Alpine A-Frame - midcentury cabin by Lake Raponda
Alpine A-Frame - midcentury cabin by Lake Raponda
Cozy Log Cabin on the River | Fireplace | Loft
Cozy Log Cabin on the River | Fireplace | Loft
10.0 out of 10, Exceptional, (5)
"The house and furnishings were clean and well organized, and the surroundings are beautiful. Hope to return!"
Cozy Log Cabin on the River | Fireplace | Loft
Cozy Mount Snow Chalet w/ Game Room & Hot Tub
Dover Vacation Rental | 4BR | 2BA | 2,500 Sq Ft | Stairs Required
Cozy Mount Snow Chalet w/ Game Room & Hot Tub
10.0 out of 10, Exceptional, (6)
"A beautiful house with plenty of room for 3 couples. A relaxing atmosphere, we all felt immediately at home. Cozy fireplace upstairs and a game room downstairs with ping pong table and video games. Great hot tub to enjoy on cool nights. Plenty of space to relax alone or as a group. The owner was super responsive with our questions and provided suggestions to make our stay more pleasant. A really great retreat to spend time with family! Looking forward to a return visit!"
Cozy Mount Snow Chalet w/ Game Room & Hot Tub
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Wilmington Vacation Rental | 3BR | 2BA | 1,266 Sq Ft | Stairs Required
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
9.8 out of 10, Exceptional, (36)
"The three kids and I enjoyed our time."
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Mount Snow Cabin with Private Hot Tub by RedAwning
Property grounds
Mount Snow Cabin with Private Hot Tub by RedAwning
3.5 star property
Mount Snow Cabin with Private Hot Tub by RedAwning
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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

Beautiful, private log cabin with huge, relaxing screened porch
Exterior
Beautiful, private log cabin with huge, relaxing screened porch
10.0 out of 10, Exceptional, (30)
"We had a wonderful, quiet and relaxing time. Plenty of rooms for every guest. The veranda is very special. We will go back again and we would recommend it. The Host, Beth, was welcoming and helpful."
Beautiful, private log cabin with huge, relaxing screened porch
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
Vernon Vacation Rental | 1BR | 1BA | 800 Sq Ft | 3 Steps Required
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
10.0 out of 10, Exceptional, (28)
"We had a wonderful time staying at the cabin. Enjoyed the space itself and the property. Quiet, private and peaceful. Looking forward to returning in the winter. "
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
VRBO Top 10 of 2024!- Copley's Lakefront Cottage on Lake Monomonac
Exterior
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
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.