Find Cabins in Old Bennington for Rent from CA $255

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Browse Select Old Bennington Cabin Rentals

Our top choices for Old Bennington cabin rentals

Florida Mountain Log Cabin!

2.0 star property
10.0 out of 10, Exceptional, (3)
"Place was super clean. Beds were comfortable. Location was great."
The price is CA $255
CA $551 total
includes taxes & fees
Sep 4 - Sep 5
Florida Mountain Log Cabin!

Mountains, pond, old barn, hiking trails- quintessential Vermont

9.4 out of 10, Exceptional, (110)
"The accommodations for our week’s vacation were awesome. The home was beautiful, the goats and chickens enjoyed by all, and the views of the autumn foliage from the back porch were amazing. "
Mountains, pond, old barn, hiking trails- quintessential Vermont

The Greylock Cabin - True Cabin in the woods on 30 acres. Pet-Friendly

The price is CA $328
CA $641 total
includes taxes & fees
Sep 2 - Sep 3
The Greylock Cabin - True Cabin in the woods on 30 acres. Pet-Friendly

Lakefront House with Stunning Views and Great Room

9.8 out of 10, Exceptional, (18)
"Beautiful setting. We had fun exploring the area and made good use of the kayaks to explore the lake."
Lakefront House with Stunning Views and Great Room

Breathtaking Mtn Views: Stylish Rustic Retreat!

10.0 out of 10, Exceptional, (29)
"The pictures of this place do not even do it justice. It was breathtaking. We had so much fun exploring Bennington during the day and returning to Big Sky to relax and enjoy the beautiful property. The house had everything we needed and more; the beds were so comfortable, and we enjoyed our time together. We will be back soon!"
Breathtaking Mtn Views: Stylish Rustic Retreat!

Trending Family Retreat- Deck-Pvt. Hot Tub -Clubhouse Pool, Game Room

10.0 out of 10, Exceptional, (23)
"We had a great time at this lovely cabin! Came well stocked and as advertised."
Trending Family Retreat- Deck-Pvt. Hot Tub -Clubhouse Pool, Game Room

Classic Vermont cabin with forest views, woodstove, pools, hot tub & gym

7.0 out of 10, Good, (7)
"The cabin was a perfect rustic experience for foliage viewing and exploring Wilmington and the nearby areas!! Everything was perfect!"
Classic Vermont cabin with forest views, woodstove, pools, hot tub & gym

Waterfalls-View-Pond. Secluded Vermont Log Cabin with EV Outlet

10.0 out of 10, Exceptional, (81)
"Perfectly clean and welcoming cabin. Comfy beds, great location. Would definitely return. "
Waterfalls-View-Pond. Secluded Vermont Log Cabin with EV Outlet

Vermont Lake Front Log Cabin Close to Mt. Snow

10.0 out of 10, Exceptional, (68)
"The property was very nice, and the host was very accommodating and responsive. Would definitely stay here again. "
Vermont Lake Front Log Cabin Close to Mt. Snow

Cozy Mountain Escape to Southern Vermont

9.6 out of 10, Exceptional, (46)
"Quick weekend getaway. Nice house and good host. "
Cozy Mountain Escape to Southern Vermont

Cozy 2-bedroom cabin near Mount Snow 3 min drive

2.0 star property
9.6 out of 10, Exceptional, (8)
"Great cabin! Perfect for our family of 4 and our dog! Very close to mount snow and walking distance to great restaurants! "
Cozy 2-bedroom cabin near Mount Snow 3 min drive

Chalet with Amazing views+ Hot Tub + privacy

10.0 out of 10, Exceptional, (2)
"Loved how quiet and private this cabin was. The bed upstairs was incredibly comfy. Stayed here in 100 degree weather and the AC was stellar. Overall, if you're staying in the area, you cant do better than this place. Owner was SUPER responsive. Highly recommend, can't think of any negatives. "
Chalet with Amazing views+ Hot Tub + privacy

The Stratton Cabin | Close to Stratton & Mt Snow!

10.0 out of 10, Exceptional, (4)
"Our stay was wonderful. The cabin is clean and fully equipped. "
The Stratton Cabin | Close to Stratton & Mt Snow!

Boulder Run Cabin-Mountain Views/Sauna/Hot Tub/EV Charger

10.0 out of 10, Exceptional, (2)
"Beautiful peaceful location in the green mountains leaf peeping would be amazing next time! Orvis Flagship store is amazing’ don’t forget the works bagel shop! Up for breakfast was ok I would try Bobs dinner next time! Bennington is a pretty drive not a great shopping area cool to see the old grave yard walking tour! Updated home with excellent deck! "
Boulder Run Cabin-Mountain Views/Sauna/Hot Tub/EV Charger

Wilmington Chalet w/ Hot Tub < 8 Mi to Mount Snow!

9.8 out of 10, Exceptional, (8)
"Perfect house in a great town would definitely stay here again"
Wilmington Chalet w/ Hot Tub < 8 Mi to Mount Snow!

Private Wooded Cabin: 7 Mi to Mount Snow!

10.0 out of 10, Exceptional, (34)
"Great central location with tons of room."
Private Wooded Cabin: 7 Mi to Mount Snow!

The Birchwood Cabin - Stunning Mountain Views

2.0 star property
10.0 out of 10, Exceptional, (2)
"This cabin was everything we could have asked for! Great, peaceful location with a beautiful view. Tastefully decorated and wonderful open concept for kitchen and living room set-up. We really enjoyed the game room downstairs, too. We will definitely be back soon."
The price is CA $408
CA $951 total
includes taxes & fees
Sep 10 - Sep 11
The Birchwood Cabin - Stunning Mountain Views

Updated Chalet. Minutes from Mt, Lakes and Golf.

8.0 out of 10, Very good, (1)
"Good stay, some difficulty getting in and out of neighborhood and no access to hot tub."
Updated Chalet. Minutes from Mt, Lakes and Golf.

Sleek Cabin w/ Deck, 8 Miles to Mount Snow & Hikes

10.0 out of 10, Exceptional, (7)
"House was very clean. Community amenities were top notch and location very convenient. Host was communicative and respectful. Will stay again!"
Sleek Cabin w/ Deck, 8 Miles to Mount Snow & Hikes

Cozy A-Frame Cabin w/ Pool Table: 8 Mi to Mt Snow!

9.8 out of 10, Exceptional, (17)
"House was great location to my snow and Stratton. It’s dog friendly which we loved brining our girl with us. The host was amazing and accommodating "
Cozy A-Frame Cabin w/ Pool Table: 8 Mi to Mt Snow!
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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Top Old Bennington Hotel Reviews