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
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

Our top choices for Bennington condo rentals

TV, fireplace

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)
"Appeared dated"
United States
John B.
$281 nightly
The price is $317
Jun 27 - Jun 28
Total with taxes and fees
Lovely ski-in/out condo steps from ski lift with trails and amazing views
Fridge, microwave, oven, stovetop

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, (31 reviews)
"Great space, great location!"
United States
Jason S.
$323 nightly
The price is $365
Jun 28 - Jun 29
Total with taxes and fees
Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub
Property grounds

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

Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Stratton
$351 nightly
The price is $396
Jun 27 - Jun 28
Total with taxes and fees
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Smart TV, fireplace

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.
$451 nightly
The price is $458
Jun 27 - Jun 28
Total with taxes and fees
New! Vermont Getaway! Stratton - close to skiing!
Lobby

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,409 reviews)
"Property is great and stay was great"
United States
Isha
$142 nightly
The price is $158
Jul 8 - Jul 9
Total with taxes and fees
Vacation Village in the Berkshires
Property grounds

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)
"Our stay was perfectly pleasant but the parking was far from the unit and the ski school and daycare was on a different part of the mountain which made the location inconvenient for having little kids with us."
United States
Teresa W.
$236 nightly
The price is $266
Jun 27 - Jun 28
Total with taxes and fees
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
TV, DVD player

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.
$205 nightly
The price is $232
Jun 28 - Jun 29
Total with taxes and fees
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
TV

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.
$383 nightly
The price is $433
Jun 27 - Jun 28
Total with taxes and fees
Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Exterior

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
$234 nightly
The price is $265
Jun 27 - Jun 28
Total with taxes and fees
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Beach

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.
$250 nightly
The price is $283
Jul 9 - Jul 10
Total with taxes and fees
Cozy 3 bedroom condo 2.5 miles to Mount Snow
Smart TV, fireplace, books

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

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Ludlow
9.8 out of 10, Exceptional, (109 reviews)
"Great location, "
United States
Bryan R J.
$268 nightly
The price is $290
Jun 30 - Jul 1
Total with taxes and fees
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Sauna

Magic Mountain Trailside Condo - Ski In / Ski Out

Magic Mountain Trailside Condo - Ski In / Ski Out
Londonderry
9.8 out of 10, Exceptional, (14 reviews)
"Nice and we enjoyed our stay"
United States
Gretchen H.
$270 nightly
The price is $305
Jun 30 - Jul 1
Total with taxes and fees
Magic Mountain Trailside Condo - Ski In / Ski Out
Lobby

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.
$281 nightly
The price is $317
Jun 30 - Jul 1
Total with taxes and fees
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
TV, DVD player, books, video library

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

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Ludlow
$331 nightly
The price is $374
Jul 1 - Jul 2
Total with taxes and fees
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Outdoor pool, a heated pool

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, (23 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.
$480 nightly
The price is $538
Jun 27 - Jun 28
Total with taxes and fees
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
TV

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
Jul 15 - Jul 16
Total with taxes and fees
Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
Marina

Mountain condo by Okemo w/ hot tub

Mountain condo by Okemo w/ hot tub
Ludlow
9.4 out of 10, Exceptional, (24 reviews)
"Good Communication, condo was clean and well stocked. Washer was out of service during our stay, but host reached out prior to notify and confirm it wouldn’t be an issue. No complaints, would stay again. "
United States
P H.
$416 nightly
The price is $467
Jun 28 - Jun 29
Total with taxes and fees
Mountain condo by Okemo w/ hot tub
Condo, 3 Bedrooms | Marina

Okemo Westwood Condo 3 Bedroom Condo by RedAwning

Okemo Westwood Condo 3 Bedroom Condo by RedAwning
3.5 star property
Ludlow
$649 nightly
The price is $707
Jun 28 - Jun 29
Total with taxes and fees
Okemo Westwood Condo 3 Bedroom Condo by RedAwning
Interior

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.
$538 nightly
The price is $607
Jun 28 - Jun 29
Total with taxes and fees
Mount Snow Condo: 4 min Walk to Sundance Lift (High Speed - 6 Seat)
Pool

Seasons Condo- Ski-on/off

Seasons Condo- Ski-on/off
Dover
$671 nightly
The price is $709
Jun 27 - Jun 28
Total with taxes and fees
Seasons Condo- Ski-on/off
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

10/10 Excellent
"Great room great staff. Love staying at Hotel Vervana"
Damian 2-night trip
Posted 20 hours ago
Hotel Vervana, Trademark Collection by Wyndham

Find out more about Bennington

Bennington Condo Rentals information

Number of reviews
2,902
Accommodation
63 Condo Rentals
Lowest Price
$158
Highest Price
$709

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.

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