Photo by Donny Campos

Search Cabin Rentals in Winchester

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 33 Cabin Rentals in Winchester with updated reviews, rates, and availability.

Mountain Views•Summer Sunsets•Private Hiking Tail•Gameroom•Minimalist

10.0 out of 10, Exceptional, (33)
"This house was the perfect family get away. My family enjoyed everything the property had to offer and also skiing close by. Amanda was very quick to respond to all my questions. Overall my family had a fantastic trip."
Mountain Views•Summer Sunsets•Private Hiking Tail•Gameroom•Minimalist

Jacksonville Cabin w/ Wraparound Deck & Views

9.6 out of 10, Exceptional, (29)
"The cabin was great, beautiful surroundings. Very nice house."
Jacksonville Cabin w/ Wraparound Deck & Views

This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!

9.8 out of 10, Exceptional, (116)
"We really enjoyed our time in Vermont. The house is beautiful post and beam construction, and the property is gorgeous. There were still a couple of feet of snow on the ground, and we used the wood stove the entire week. We only saw one car drive by the entire week- very secluded. The internet is extremely fast, which allowed me to work while we were there, but also get away from the city, which is exactly what we were looking for. The property was safe for our dogs to roam as well, which was...
This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!

Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

9.8 out of 10, Exceptional, (10)
"The host was amazing. Very kind and very responsive! Made great suggestions for places to eat. The property is quiet and great for relaxation! 10/10 will stay agin! "
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

Cozy Log Cabin on the River | Fireplace | Loft

10.0 out of 10, Exceptional, (10)
"We booked this property for a ski vacation over kids winter break, and found it was perfect for our needs. Very clean property, modern appliances in well-equipped kitchen, loft area the kids loved and full of games, plenty of hot water and good temperature control throughout the home, beautiful private master suite, and functional fireplace with plenty of firewood. Easy 25 minute drive to Mt. Snow. Owner was very communicative with a guide and daily check-ins. Property is well-maintained,...
Cozy Log Cabin on the River | Fireplace | Loft

Cozy Updated Log Cabin with Mountain Views close to Monadnock

9.6 out of 10, Exceptional, (23)
"Nice cabin with privacy "
Cozy Updated Log Cabin with Mountain Views close to Monadnock

Charming Lake Cottage est 1903! Private and relaxing waterfront, family fun!

9.8 out of 10, Exceptional, (51)
"How wonderful is this cabin. The perfect trade-off between being remote and in nature, but in a super cozy, well equipped, and super comfortable house! We hope we will be back to enjoy another time… Landlord / manager were excellent in communication, and very flexible. Thank you "
Charming Lake Cottage est 1903! Private and relaxing waterfront, family fun!

Cozy Mount Snow Chalet w/ Game Room & Hot Tub

10.0 out of 10, Exceptional, (11)
"We loved the cabin and got a lot of great use out of the hot tub! Owner was very communicative when I had questions. "
Cozy Mount Snow Chalet w/ Game Room & Hot Tub

Cozy Cabin Retreat on Putney Mountain

10.0 out of 10, Exceptional, (2)
"Pleasant arrival and departure easy to find and is in a great location feeling like your in nature but not too far from a quaint town. What a peaceful warm setting. The home has some of the nicest touches that make you feel very comfortable and cozy. It is so quiet and yet you don’t feel too isolated! Hiking close by was simple and fun. I can’t wait to come back to explore more of the property after spring has spring. I can totally see hosting a retreat in this type of space and for now my own...
Cozy Cabin Retreat on Putney Mountain

Hike & Swim On-Site: Cozy Falls Brook Cabin

10.0 out of 10, Exceptional, (10)
"Great little cabin, would definitely stay again!"
Hike & Swim On-Site: Cozy Falls Brook Cabin

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

10.0 out of 10, Exceptional, (51)
"Would recommend if anyone wants a quiet, peaceful getaway."
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT

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

10.0 out of 10, Exceptional, (35)
"My husband and I absolutely loved our stay. Such care and love has gone into Fiddlers Rest. Lulu spoke to my husband and she was absolutely lovely.The fog was thick and it rained. We built a fire and my husband finished a book! We explored in the rain and love all the treasures on the land.We did have a problem with the sight on paying for our pet. We texted and called and made the decision to bring her. Lulu told us to leave the money and a note, so it all worked out.Thank-you for your...
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!

Alpine A-Frame - midcentury cabin by Lake Raponda

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

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! "
The price is AED 566
AED 1,442 total
includes taxes & fees
19 Apr - 20 Apr
Cozy Log Cabin - Dog Friendly

Beautiful Lakefront Log Cabin 15 Minutes from Mount Snow

10.0 out of 10, Exceptional, (12)
"We absolutely loved the home! We couldn’t have had a better family trip! The location was great for the ski mountain. The space accommodated us nicely. We will definitely stay again if we have the chance! I highly recommend this amazing home!! "
Beautiful Lakefront Log Cabin 15 Minutes from Mount Snow

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

10.0 out of 10, Exceptional, (13)
"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!

Cabin Retreat in Southern Vermont

8.4 out of 10, Very Good, (6)
"Property very much as advertised.If you read reviews, there are window coverings that face the owners house, but it's not like you're on top of them. A lot of space separates you.Wood stove is great.Hot tub is on the back of cabin facing the woods.Steps are steep to get to the second floor, but easy to navigate. If you have a larger pup, they wont be able to get up there.My husband is already trying to plan when we go back.Very cute place, a few restaurants locally, but very quiet area to...
Cabin Retreat in Southern Vermont

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!

Log Cabin w/ Amazing Views, River Frontage & Hot Tub

10.0 out of 10, Exceptional, (26)
"Our second stay. A wonderful property and location. Thank you Lasse. "
Log Cabin w/ Amazing Views, River Frontage & Hot Tub

Wellness Getaway with a Personal Sauna, and Private River Beach!

2.0 star property
10.0 out of 10, Exceptional, (1)
"The folks are SUPER and made me feel very welome"
The price is AED 466
AED 2,032 total
includes taxes & fees
21 Apr - 22 Apr
Wellness Getaway with a Personal Sauna, and Private River Beach!
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.
Don't see what you're looking for?
See all available properties in Winchester
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Winchester

GAMERS HAVEN, River Wine Inn!

2.0 star property
10.0 out of 10, Exceptional, (11)
"Great place with an elite game room. "
GAMERS HAVEN, River Wine Inn!

The Jelly Mill-A River Retreat

10.0 out of 10, Exceptional, (47)
"Was exactly as described. Had everything we needed and more. Only thing we had hoped for that wasn’t there was some olive oil, so bring your own if you want to cook. Not quite as remote as we were anticipating, but in a good way . Was still very rural, and we were grateful for the 4wheel drive vehicle we rented. Perfect, majestic, natural location for our family retreat."
The Jelly Mill-A River Retreat

Riverfront 2 Bedroom Unit 2

9.6 out of 10, Exceptional, (17)
"Overall, not bad. The host seems thoughtful about what the leave for you to use, but the apartment and exterior could use some TLC"
Riverfront 2 Bedroom Unit 2
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.