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

Search Condos Rentals in Bennington from CA $330

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Bennington condo rentals

A living room with a sofa, a television, a fireplace, and a dining area with chairs and a table.

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 $106
CA $451 total
includes taxes & fees
Oct 27 - Oct 28
Lovely ski-in/out condo steps from ski lift with trails and amazing views
A modern kitchen with dark cabinetry, stainless steel appliances, and a bar area with stools.

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, (37 reviews)
"Great space, great location!"
United States
Jason S.
The price is CA $296
CA $747 total
includes taxes & fees
Oct 19 - Oct 20
Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub
A multi-story building with a stone facade, a central courtyard with a hot tub, and a stone pathway.

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 $199
CA $578 total
includes taxes & fees
Oct 27 - Oct 28
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
A modern living room with a fireplace, a large sofa set, and a view through the glass doors.

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 $584
CA $913 total
includes taxes & fees
Nov 1 - Nov 2
New! Vermont Getaway! Stratton - close to skiing!
A calm lake with a wooden boat on the shore.

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)
"The place was absolutely relaxing, clean, and one of the best host we’ve ever had an experience with. Will come back!!"
United States
Scott S.
The price is CA $143
CA $444 total
includes taxes & fees
Nov 1 - Nov 2
Cozy 3 bedroom condo 2.5 miles to Mount Snow
A spacious living area with a high ceiling, wooden beams, a fireplace, and a large wooden coffee table.

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 $149
CA $514 total
includes taxes & fees
Oct 24 - Oct 25
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
A spacious living area with a red sofa, wooden staircase, and a kitchen with a bar.

7. Walk to Mt Snow Lifts • Sleeps 8 • Fireplace, Hot Tub, Sauna, Pool • 2BR/2BA

Walk to Mt Snow Lifts • Sleeps 8 • Fireplace, Hot Tub, Sauna, Pool • 2BR/2BA
Dover
10.0 out of 10, Exceptional, (1 review)
"Incredible views, immaculate, spacious, fully sticked kitchen, great pool and amenities. Easy access with great communication from the host. 10/10 recommend"
United States
Danielle F.
The price is CA $179
CA $508 total
includes taxes & fees
Oct 15 - Oct 16
Walk to Mt Snow Lifts • Sleeps 8 • Fireplace, Hot Tub, Sauna, Pool • 2BR/2BA
An indoor swimming pool with a tiled floor, a pool table, and a bar area.

8. Mountainside Condo - Front-Door Shuttle & Indoor Pool Complex

Mountainside Condo - Front-Door Shuttle & Indoor Pool Complex
Dover
9.6 out of 10, Exceptional, (5 reviews)
"Property is very clean, beautiful condo and scenery, owner was great and communication was incredible! Highly recommend, great stay!"
United States
Douglas D.
The price is CA $194
CA $611 total
includes taxes & fees
Oct 27 - Oct 28
Mountainside Condo - Front-Door Shuttle & Indoor Pool Complex
A cozy cabin interior with a sofa, dining table, chairs, wooden cabinets, and a kitchen area.

9. 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 $79
CA $421 total
includes taxes & fees
Oct 27 - Oct 28
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
A view of a grassy area with a ski lift and a building in the background.

10. 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)
"It was a perfect location and had everything we needed for a great stay."
United States
Danna K.
The price is CA $106
CA $379 total
includes taxes & fees
Oct 27 - Oct 28
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
A living room with a sofa, a bench, a fireplace, a TV, and a large window.

11. 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)
"Great property, clean and close to the slope"
United States
tiliger01
The price is CA $73
CA $330 total
includes taxes & fees
Oct 27 - Oct 28
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
A kitchen counter with a bottle of Cabernet Sauvignon, a feedback card, and a basket of fruits.

12. Mount Snow Fireplace Condo - 5-10 Min Walk to Sundance Lift - Sleeps 8

Mount Snow Fireplace Condo - 5-10 Min Walk to Sundance Lift - Sleeps 8
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 $369
CA $938 total
includes taxes & fees
Oct 15 - Oct 16
Mount Snow Fireplace Condo - 5-10 Min Walk to Sundance Lift - Sleeps 8
A two-story house with a porch, a staircase, and a front door.

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

Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Ludlow
8.8 out of 10, Excellent, (27 reviews)
"You better ask for one of the rear units because the front one is practically in the middle of the road. It’s noisy. It’s dingy, the owner refused to let us check in an hour early, which actually worked out in our favor since we didn’t want to stay there after we saw the place. We asked to move to a rear unit. The answer was no. We didn’t ask for a refund. We just went and booked another room and left this place empty for the night. There are so many other nice places to stay in this area. I...
United States
William
The price is CA $149
CA $386 total
includes taxes & fees
Oct 27 - Oct 28
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
A spacious living room with a stone fireplace, wooden furniture, and large windows.

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.
The price is CA $261
CA $983 total
includes taxes & fees
Nov 13 - Nov 14
Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
A modern living room with a fireplace, a television, and a ceiling fan.

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.
The price is CA $261
CA $726 total
includes taxes & fees
Oct 27 - Oct 28
Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Wake up to breathtaking mountain views and slopeside convenience at this cozy retreat, where adventure and relaxation go hand in hand.

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

Expansive 2BR | Sleeps 10 | Ski-In
West Dover
The price is CA $663
CA $827 total
includes taxes & fees
Oct 19 - Oct 20
Expansive 2BR | Sleeps 10 | Ski-In
A multi-story building with a red and yellow facade, surrounded by lush greenery and flowering plants.

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

Okemo | Charming 1BR Condo + Close to Amenities
Jackson Gore Base Area
The price is CA $437
CA $551 total
includes taxes & fees
Oct 27 - Oct 28
Okemo | Charming 1BR Condo + Close to Amenities
A rectangular pool with a glass enclosure, surrounded by lounge chairs and umbrellas, set in a landscaped area with trees.

18. 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 $427
CA $774 total
includes taxes & fees
Oct 27 - Oct 28
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
A two-story house with a covered porch, a staircase, and a front door with a wreath.

19. 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 $142
CA $375 total
includes taxes & fees
Oct 27 - Oct 28
2nd-floor downtown Ludlow studio condo with kitchenette, streaming
A two-story house with a covered porch, a staircase, and a front door with a wreath.

20. Condo in the heart of town near skiing - less than a mile to Okemo Mountain

Condo in the heart of town near skiing - less than a mile to Okemo Mountain
Ludlow
9.0 out of 10, Wonderful, (14 reviews)
"Great place!"
United States
Darcie L.
The price is CA $187
CA $459 total
includes taxes & fees
Oct 27 - Oct 28
Condo in the heart of town near skiing - less than a mile to Okemo Mountain
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Bennington Hotel Reviews

Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham

8/10 Good
"Pet friendly…if you are in building 3 you are pretty far from breakfast and lobby"
teresa 1-night trip
Posted 8 hours ago
Hotel Vervana, Trademark Collection by Wyndham

Find out more about Bennington

Bennington Condo Rentals information

Number of reviews
376
Accommodation
71 Condo Rentals
Lowest Price
CA $330
Highest Price
CA $988

Frequently asked questions

Why book your condo in Bennington with Expedia?
We think that vacations shouldn't be hard, so if you're searching for condos at an affordable rate, Expedia has your back. Save cash and go for something small and affordable, or splurge on a luxury condo and spoil the ones you love most. Take advantage of our search filters to find a place in Bennington that suits your style.
How can I find cheap condos in Bennington?
With Expedia's helpful filter tool, getting your hands on cheap condos in Bennington couldn't be simpler. To find properties that'll make your wallet smile, refine your search by budget, star rating and amenities.
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.

Explore a world of travel with Expedia