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Compare 23 Cabin Rentals in Winchester with updated reviews, rates, and availability.

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, (48)
"Peaceful, beautiful property. Was a relaxing stay, had everything we needed. "
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna
Room

Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

9.8 out of 10, Exceptional, (6)
"Our two night stay was great. Loved how close it was to the bike path and the fire pit in the back. Clare was very responsive!"
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna
Cozy Log Cabin on the River | Fireplace | Loft

Cozy Log Cabin on the River | Fireplace | Loft

10.0 out of 10, Exceptional, (6)
"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
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, (7)
"Very nice location and getaway. Would highly recommend for anyone looking for a refreshing getaway. "
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, (38)
"Quaint cozy spot. Well cared for. Relaxing family time."
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
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, (27)
"We enjoyed our stay. Everything was clean. The only thing I would suggest is checking the stairs to the basement. "
Jacksonville Cabin w/ Wraparound Deck & Views
Charming & Cozy River Front Cabin- Close to ski mountains. Ski,Fish,Swim & Hike!
Exterior 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, (9)
"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 - Dog Friendly
Exterior

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!
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, (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 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, (29)
"Absolutely gorgeous mountain view, beautiful cabin, fully stocked kitchen, loved the hiking trails! Owners thought of every little detail to make it feel like home away from home. "
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, (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
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
Living area

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
Exterior

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
Welcome to the Alpine A-frame!

Alpine A-Frame - midcentury cabin by Lake Raponda

2.0 out of 10, (1)
Alpine A-Frame - midcentury cabin by Lake Raponda
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, (5)
"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
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
Spacious Wilmington Cabin: Walk to Lake
Wilmington Vacation Rental | 4BR | 3BA | Step-Free Entry | 2,662 Sq Ft

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

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

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

9.0 out of 10, Wonderful, (42)
"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
Exterior

Charming Waterfront Log Cabin

9.4 out of 10, Exceptional, (36)
"We really appreciated the solitude and quiet retreat this cabin offered. "
Charming Waterfront Log Cabin
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, (48)
"Peaceful, beautiful property. Was a relaxing stay, had everything we needed. "
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
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.