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Condo Rentals in Bennington

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

8.8 out of 10, Excellent, (23)
"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."
$261 nightly
The price is $295
Jun 23 - Jun 24
Total includes taxes and fees
Lovely ski-in/out condo steps from ski lift with trails and amazing views

Charming One-Bedroom Condo on Bromley Mountain

10.0 out of 10, Exceptional, (2)
"There is no place I’d rather stay in VT. It’s a perfect condo and the recent renovations are really nice. It’s got all the comforts of home and great touches throughout. Bromley is a great community to be in, it’s close to town, obviously the slopes, and just a overall stay!"
$296 nightly
The price is $334
Jun 23 - Jun 24
Total includes taxes and fees
Charming One-Bedroom Condo on Bromley Mountain

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

7.4 out of 10, Good, (17)
"Proximity to southern Vermont towns, and shopping and dining in the village."
$331 nightly
The price is $374
Jun 23 - Jun 24
Total includes taxes and fees
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities

Stratton Mtn Studio | Renovated | Walk to Lifts

10.0 out of 10, Exceptional, (28)
"Great location."
$357 nightly
The price is $403
Jun 23 - Jun 24
Total includes taxes and fees
Stratton Mtn Studio | Renovated | Walk to Lifts

New! Vermont Getaway! Stratton - close to skiing!

2.0 star property
$613 nightly
The price is $621
Jun 23 - Jun 24
Total includes taxes and fees
New! Vermont Getaway! Stratton - close to skiing!

Perfect location for your next Vermont Getaway!

9.2 out of 10, Wonderful, (5)
"The condo was extremely nice, very clean and in great shape. The rooms and bathrooms are very spacious, well furnished and appointed; the layout was great. The check in and out process was very simple and easy. It is short walk (2 min) to the village and 5 min to the slopes. Highly recommend, one of the best places we’ve ever stayed!"
$620 nightly
The price is $684
Jun 23 - Jun 24
Total includes taxes and fees
Perfect location for your next Vermont Getaway!

Cozy 4-bedroom condo with AC, WiFi in charming Stratton

$1,171 nightly
The price is $1,323
Jun 23 - Jun 24
Total includes taxes and fees
Cozy 4-bedroom condo with AC, WiFi in charming Stratton

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

10.0 out of 10, Exceptional, (18)
"Lovely large property, everything was clean and well maintained! Will happily stay there again!"
$482 nightly
The price is $540
Jun 23 - Jun 24
Total includes taxes and fees
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

10.0 out of 10, Exceptional, (95)
"We loved Wendy's place. It was clean, updated and had everything we needed. Its in the center of town so convenient to shops and restaurants and close to the mountain. We will be booking again. "
$245 nightly
The price is $265
Jul 7 - Jul 8
Total includes taxes and fees
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

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

9.0 out of 10, Wonderful, (13)
"Great location and very comfortable."
$223 nightly
The price is $252
Jul 15 - Jul 16
Total includes taxes and fees
Condo in the heart of town near skiing - less than a mile to Okemo Mountain

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

9.0 out of 10, Wonderful, (72)
"Dated but well appointed and comfortable condo. Be prepared for lots of stairs but great location directly slopeside."
$238 nightly
The price is $266
Jun 23 - Jun 24
Total includes taxes and fees
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

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

9.4 out of 10, Exceptional, (24)
"Great location for ski in ski out unit on 1st floor. Steps away from clock tower base and lift. Easy access to post ski fun for drink/dining super close The Loft or The Bull both 2 mins walk from condo. "
$205 nightly
The price is $230
Jun 23 - Jun 24
Total includes taxes and fees
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Ground Floor ski-in/out condo, full kitchen & high-speed WiFi

9.4 out of 10, Exceptional, (20)
"Enjoy our stay !!!!! Awesome in and out right on the slope feet away for deck."
$348 nightly
The price is $390
Jun 23 - Jun 24
Total includes taxes and fees
Ground Floor ski-in/out condo, full kitchen & high-speed WiFi

Okemo | Charming 1BR Condo + Close to Amenities

$279 nightly
The price is $305
Jun 24 - Jun 25
Total includes taxes and fees
Okemo | Charming 1BR Condo + Close to Amenities

Okemo | 1BR + Loft Condo + Close to All Amenities

$317 nightly
The price is $346
Jun 24 - Jun 25
Total includes taxes and fees
Okemo | 1BR + Loft Condo + Close to All Amenities

Okemo | 3BR Condo & Close to Amenities + Slopes!

$411 nightly
The price is $450
Jun 24 - Jun 25
Total includes taxes and fees
Okemo | 3BR Condo & Close to Amenities + Slopes!

Okemo | 3BR + Loft Condo & Close to All Amenities

$564 nightly
The price is $617
Jun 24 - Jun 25
Total includes taxes and fees
Okemo | 3BR + Loft Condo & Close to All Amenities

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

7.6 out of 10, Good, (53)
"This cozy cabin was perfect for a ski weekend with friends. We really enjoyed gathering by the stone fireplace after a couple long days out on the slopes."
$245 nightly
The price is $275
Jun 23 - Jun 24
Total includes taxes and fees
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

Cozy 3 bedroom condo 2.5 miles to Mount Snow

9.2 out of 10, Wonderful, (39)
"This is the third time I’ve stayed here and it’s very convenient and I really love what the host did for upgrades on the property. "
$263 nightly
The price is $297
Jun 30 - Jul 1
Total includes taxes and fees
Cozy 3 bedroom condo 2.5 miles to Mount Snow

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

9.8 out of 10, Exceptional, (16)
"Location location location!"
$357 nightly
The price is $400
Jun 23 - Jun 24
Total includes taxes and fees
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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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.