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Our top choices for Bennington condo rentals

8.6 out of 10, Excellent, (27)
"We loved staying at the townhome. It was a welcome place to stay while we traveled around, enjoying fall. It was very comfortable and the village amenities were great."
United States
John N.
The price is AED 470
AED 1,536 total
includes taxes & fees
6 Jan - 7 January 2026
Lovely ski-in/out condo steps from ski lift with trails and amazing views
7.4 out of 10, Good, (20)
"A great weekend. The property was clean and comfortable."
United States
Joan P.
The price is AED 588
AED 1,596 total
includes taxes & fees
12 Jan - 13 January 2026
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
10.0 out of 10, Exceptional, (30)
"Great location."
United States
Jeffrey
The price is AED 1,539
AED 2,652 total
includes taxes & fees
5 Jan - 6 January 2026
Stratton Mtn Studio | Renovated | Walk to Lifts
2.0 star property
The price is AED 2,512
AED 4,204 total
includes taxes & fees
1 Jan - 2 January 2026
Chic Condo <1 Mile Away from Stratton’s Village
9.2 out of 10, Wonderful, (5)
"Perfect location and nice condo"
United States
Doug M.
The price is AED 1,846
AED 3,411 total
includes taxes & fees
5 Jan - 6 January 2026
Perfect location for your next Vermont Getaway!
3.0 star property
8.8 out of 10, Excellent, (2194)
"I great place to stay!!"
United Kingdom
Maricel
The price is AED 382
AED 467 total
includes taxes & fees
4 Jan - 5 January 2026
Vacation Village in the Berkshires
9.2 out of 10, Wonderful, (26)
"Loved the location"
United States
Steven W.
The price is AED 654
AED 1,529 total
includes taxes & fees
28 Jan - 29 January 2026
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
9.0 out of 10, Wonderful, (74)
"Perfect location for a quick ski trip. "
United States
Michael D.
The price is AED 367
AED 1,176 total
includes taxes & fees
11 Jan - 12 January 2026
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
8.8 out of 10, Excellent, (32)
"Very nice accommodations and location!"
United States
Michael M.
The price is AED 599
AED 1,678 total
includes taxes & fees
21 Jan - 22 January 2026
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
8.6 out of 10, Excellent, (4)
"Great location and convenient to all local businesses. I enjoyed it very much. Would stay here anytime and plan to again. "
United States
Kevin C.
The price is AED 474
AED 1,113 total
includes taxes & fees
5 Jan - 6 January 2026
2nd-floor downtown Ludlow studio condo with kitchenette, streaming
8.6 out of 10, Excellent, (14)
"Excellent Location.. "
United States
Juan Carlos L.
The price is AED 426
AED 1,245 total
includes taxes & fees
4 Jan - 5 January 2026
Ski-in/out mountainside condo with balcony, washer/dryer & high-speed WiFi
10.0 out of 10, Exceptional, (102)
"Convenient 2 BR space with comfy beds right in the heart of Ludlow. Would definitely stay there again."
United States
Andrew L.
The price is AED 698
AED 1,299 total
includes taxes & fees
12 Jan - 13 January 2026
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
9.0 out of 10, Wonderful, (46)
"Great quiet location, kitchen had enough essentials for basic cooking to be easy. The king bed was comfortable and the living room is a great hangout spot."
United States
Franklin C.
The price is AED 367
AED 1,129 total
includes taxes & fees
14 Jan - 15 January 2026
Cozy 3 bedroom condo 2.5 miles to Mount Snow
7.6 out of 10, Good, (53)
"Irish Bar nearby was a plus on St. Patrick’s Day !"
United States
Warren
The price is AED 342
AED 1,401 total
includes taxes & fees
13 Jan - 14 January 2026
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
9.4 out of 10, Exceptional, (22)
"Enjoy our stay !!!!! Awesome in and out right on the slope feet away for deck."
United States
Dan G.
The price is AED 650
AED 1,621 total
includes taxes & fees
8 Jan - 9 January 2026
Ground Floor ski-in/out condo, full kitchen & high-speed WiFi
9.0 out of 10, Wonderful, (14)
"Great location and very comfortable."
United States
Richard J.
The price is AED 518
AED 1,298 total
includes taxes & fees
13 Jan - 14 January 2026
Condo in the heart of town near skiing - less than a mile to Okemo Mountain
9.0 out of 10, Wonderful, (22)
"Great rate for a place with all the basics!"
United States
Macgregor
The price is AED 474
AED 1,113 total
includes taxes & fees
5 Jan - 6 January 2026
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
10.0 out of 10, Exceptional, (19)
"Amazing place! "
United States
Tara
The price is AED 1,102
AED 1,979 total
includes taxes & fees
4 Jan - 5 January 2026
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
10.0 out of 10, Exceptional, (14)
"Clean, comfortable place with nice amenities. "
United States
Mike H.
The price is AED 592
AED 1,424 total
includes taxes & fees
8 Jan - 9 January 2026
UNIQUE - 1BR Country Condo @ Jiminy Peak
9.8 out of 10, Exceptional, (16)
"Perfect spot to jump onto the mountain and ski. Two adults and 4 kids, and we had plenty of space for a long weekend."
United States
Allison T.
The price is AED 1,847
AED 3,615 total
includes taxes & fees
13 Jan - 14 January 2026
Ski-In/Out Condo with Mountain Views, and Washer/Dryer
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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