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

TV, fireplace

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, (35 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.
$281 nightly
The price is $317
Aug 26 - Aug 27
Total with taxes and fees
Lovely ski-in/out condo steps from ski lift with trails and amazing views
Coffee/tea maker, fridge, microwave, oven

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, (32 reviews)
"Great space, great location!"
United States
Jason S.
$352 nightly
The price is $397
Aug 26 - Aug 27
Total with taxes and fees
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)
$360 nightly
The price is $406
Aug 26 - Aug 27
Total with taxes and fees
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Smart TV, fireplace

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.
$457 nightly
The price is $464
Aug 26 - Aug 27
Total with taxes and fees
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.
$253 nightly
The price is $286
Aug 31 - Sep 1
Total with taxes and fees
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.
$320 nightly
The price is $362
Aug 26 - Aug 27
Total with taxes and fees
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.
$549 nightly
The price is $620
Aug 26 - Aug 27
Total with taxes and fees
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)
"Good stay. Convenient to ski slopes. Thankful for Pet Friendly."
United States
Jim H.
$320 nightly
The price is $358
Sep 22 - Sep 23
Total with taxes and fees
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.
$236 nightly
The price is $266
Aug 26 - Aug 27
Total with taxes and fees
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
TV, DVD player, books, video library

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

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Ludlow
$256 nightly
The price is $289
Aug 26 - Aug 27
Total with taxes and fees
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Outdoor dining

11. 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.
$329 nightly
The price is $368
Sep 9 - Sep 10
Total with taxes and fees
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
TV, DVD player

12. 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.
$204 nightly
The price is $231
Aug 31 - Sep 1
Total with taxes and fees
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Exterior

13. 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
$240 nightly
The price is $271
Aug 26 - Aug 27
Total with taxes and fees
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
TV

14. 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)
"convenient to okemo"
United States
marcus l.
$618 nightly
The price is $692
Aug 26 - Aug 27
Total with taxes and fees
Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
TV

15. 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.
$381 nightly
The price is $430
Sep 7 - Sep 8
Total with taxes and fees
Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Exterior

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

Expansive 2BR | Sleeps 10 | Ski-In
West Dover
$489 nightly
The price is $540
Aug 26 - Aug 27
Total with taxes and fees
Expansive 2BR | Sleeps 10 | Ski-In
Outdoor pool, a heated pool

17. 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.
$486 nightly
The price is $544
Aug 26 - Aug 27
Total with taxes and fees
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Outdoor dining

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

Okemo | Charming 1BR Condo + Close to Amenities
Jackson Gore Base Area
$323 nightly
The price is $357
Aug 26 - Aug 27
Total with taxes and fees
Okemo | Charming 1BR Condo + Close to Amenities
Indoor pool

19. 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
$743 nightly
The price is $840
Aug 26 - Aug 27
Total with taxes and fees
Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!
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.
$228 nightly
The price is $258
Aug 26 - Aug 27
Total with taxes and fees
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

South Shire

South Shire

10/10 Excellent
"Super charming Victorian home. Perfect spot to disconnect and enjoy a restful stay"
Maria Belinda 1-night trip
Posted 11 hours ago
South Shire

Find out more about Bennington

Bennington Condo Rentals information

Number of reviews
435
Accommodation
73 Condo Rentals
Lowest Price
$231
Highest Price
$840

Frequently asked questions

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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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