A covered bridge with a sign reading "Silk Road Bridge" and a height restriction of 10 feet 6 inches.

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Bennington condo rentals

Living area

1. Lovely ski-in/out condo steps from ski lift with trails and amazing views

Lovely ski-in/out condo steps from ski lift with trails and amazing views
Stratton
8.4 out of 10, Very good, (36 reviews)
"I have stayed in this condo a few times now, and for my needs it is a great value; affordable, comfortable and ideal location. "
United States
eric m.
The price is CA $103
CA $436 total
includes taxes & fees
Aug 30 - Aug 31
Lovely ski-in/out condo steps from ski lift with trails and amazing views
Private kitchen

2. Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub

Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub
Stratton Mountain
10.0 out of 10, Exceptional, (33 reviews)
"Great space, great location!"
United States
Jason S.
The price is CA $218
CA $549 total
includes taxes & fees
Aug 30 - Aug 31
Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub
Property grounds

3. Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities

Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Stratton
8.0 out of 10, Very good, (1 review)
The price is CA $193
CA $561 total
includes taxes & fees
Aug 30 - Aug 31
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Living area

4. New! Vermont Getaway! Stratton - close to skiing!

New! Vermont Getaway! Stratton - close to skiing!
Winhall
10.0 out of 10, Exceptional, (1 review)
"The place was perfect for us! Easy stay. Very clean and the wood burning fireplace was great. Would def recommend!"
United States
Carolyn K.
The price is CA $348
CA $643 total
includes taxes & fees
Aug 30 - Aug 31
New! Vermont Getaway! Stratton - close to skiing!
Beach

5. Cozy 3 bedroom condo 2.5 miles to Mount Snow

Cozy 3 bedroom condo 2.5 miles to Mount Snow
West Dover
9.2 out of 10, Wonderful, (52 reviews)
"Fire place was awesome! Great place to stay! Had everything in the kitchen we needed. All the beds were comfy! "
United States
Susan S.
The price is CA $125
CA $409 total
includes taxes & fees
Sep 8 - Sep 9
Cozy 3 bedroom condo 2.5 miles to Mount Snow
Lobby

6. Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Dover
8.6 out of 10, Excellent, (37 reviews)
"Location was fantastic! Great ski-in, ski-out location! Unit itself was very dated but location made up for it."
United States
Evan C.
The price is CA $145
CA $500 total
includes taxes & fees
Aug 30 - Aug 31
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Interior

7. Mount Snow Condo: 4 min Walk to Sundance Lift (High Speed - 6 Seat)

Mount Snow Condo: 4 min Walk to Sundance Lift (High Speed - 6 Seat)
Dover
9.4 out of 10, Exceptional, (23 reviews)
"Great location, comfortable and spacious living room and bedrooms. "
United States
Emma C.
The price is CA $294
CA $826 total
includes taxes & fees
Aug 31 - Sep 1
Mount Snow Condo: 4 min Walk to Sundance Lift (High Speed - 6 Seat)
Pool

8. 2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Hancock
9.8 out of 10, Exceptional, (6 reviews)
The price is CA $233
CA $471 total
includes taxes & fees
Aug 31 - Sep 1
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Property grounds

9. Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Clock Tower Base Area
8.8 out of 10, Excellent, (81 reviews)
"Lots of steps but great space. Blankets were dirty, which was the only downside. "
United States
serena m.
The price is CA $103
CA $366 total
includes taxes & fees
Aug 30 - Aug 31
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Living area

10. Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Clock Tower Base Area
9.2 out of 10, Wonderful, (30 reviews)
"The slope side condo was wonderful, warm and had everything we needed. Thank you, Amy"
United States
AMY K.
The price is CA $71
CA $318 total
includes taxes & fees
Aug 31 - Sep 1
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Living area

11. Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Ludlow
The price is CA $77
CA $398 total
includes taxes & fees
Aug 30 - Aug 31
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Outdoor dining

12. 2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Hancock
7.6 out of 10, Good, (13 reviews)
"Great location, right on the mountain's property "
United States
J S.
The price is CA $259
CA $497 total
includes taxes & fees
Sep 9 - Sep 10
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Living area

13. Ski-In/Out Condo with Mountain Views, and Washer/Dryer

Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Ludlow
9.6 out of 10, Exceptional, (18 reviews)
"Very clean and comfortable for our family of 4. Great ski-in/ski-out location - easily accessible to all lifts. Highly recommend. "
United States
Carey S.
The price is CA $183
CA $595 total
includes taxes & fees
Sep 7 - Sep 8
Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Exterior

14. Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Ludlow
9.0 out of 10, Wonderful, (26 reviews)
"Great location - walkable to small town. Very close drive to slopes"
United States
Keath
The price is CA $145
CA $373 total
includes taxes & fees
Aug 30 - Aug 31
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Exterior

15. Expansive 2BR | Sleeps 10 | Ski-In

Expansive 2BR | Sleeps 10 | Ski-In
West Dover
The price is CA $593
CA $744 total
includes taxes & fees
Sep 9 - Sep 10
Expansive 2BR | Sleeps 10 | Ski-In
Pool

16. Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Cavendish
10.0 out of 10, Exceptional, (24 reviews)
"Great location, and comfortable for the whole family. Everyone in the enjoyed the open living room and dining room, plus the privacy of their own bedroom space. "
United States
Ania H.
The price is CA $416
CA $746 total
includes taxes & fees
Aug 31 - Sep 1
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Living area

17. Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck

Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
Plymouth
9.8 out of 10, Exceptional, (24 reviews)
The price is CA $255
CA $958 total
includes taxes & fees
Sep 6 - Sep 7
Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
Pool

18. Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!

Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!
Okemo Village
10.0 out of 10, Exceptional, (64 reviews)
"The host is extremely friendly and accommodating! The place is large and didn’t feel cramped with two adults and five male teenagers! Perfect in every way, clean, well stocked, and easy access to the slopes!"
United States
Nina
The price is CA $623
CA $1,163 total
includes taxes & fees
Aug 30 - Aug 31
Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!
Outdoor dining

19. Okemo | Charming 1BR Condo + Close to Amenities

Okemo | Charming 1BR Condo + Close to Amenities
Jackson Gore Base Area
The price is CA $425
CA $530 total
includes taxes & fees
Aug 31 - Sep 1
Okemo | Charming 1BR Condo + Close to Amenities
Exterior

20. 2nd-floor downtown Ludlow studio condo with kitchenette, streaming

2nd-floor downtown Ludlow studio condo with kitchenette, streaming
Ludlow
8.6 out of 10, Excellent, (4 reviews)
"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 CA $138
CA $354 total
includes taxes & fees
Aug 31 - Sep 1
2nd-floor downtown Ludlow studio condo with kitchenette, streaming
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 Bennington Hotel Reviews

Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham

8/10 Good
"Nice staff. Dirty pool. Rooms were okay."
Taylor 1-night trip
Posted 2 days ago
Hotel Vervana, Trademark Collection by Wyndham

Find out more about Bennington

Bennington Condo Rentals information

Number of reviews
472
Accommodation
73 Condo Rentals
Lowest Price
CA $318
Highest Price
CA $1,163

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What is there to do in Bennington near my condo?
Whatever your tastes or interests, Bennington has tons of things to keep you on the hop. Harmen Hills Trail, Bennington Museum and Bennington Potters Yard are on most travelers' lists. Don't miss Bennington Arts Guild Gallery, Bennington Battle Monument and Hemmings Motor News Car Lover's Convenience Store & Vehicle Display either. With Expedia's Bennington condo deals, you can see more fantastic attractions like these with the money you save.

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