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 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

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)
"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.
$293 nightly
The price is $331
Jul 14 - Jul 15
Total with taxes and fees
Lovely ski-in/out condo steps from ski lift with trails and amazing views
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
Jul 14 - Jul 15
Total with taxes and fees
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
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.
$352 nightly
The price is $397
Jul 14 - Jul 15
Total with taxes and fees
Sunrise at Stratton by Sunapee Stays - walk to lifts | pool | hot tub
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.
$454 nightly
The price is $461
Jul 15 - Jul 16
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, (2,444 reviews)
"Great and tranquil location, good sleeps, friendly and helpful staff, would do it again."
United States
Melanie
$145 nightly
The price is $162
Jul 14 - Jul 15
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)
"Lots of steps but great space. Blankets were dirty, which was the only downside. "
United States
serena m.
$236 nightly
The price is $266
Jul 14 - Jul 15
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.
$217 nightly
The price is $245
Jul 21 - Jul 22
Total with taxes and fees
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
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.
$320 nightly
The price is $362
Jul 14 - Jul 15
Total with taxes and fees
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Exterior

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
Jul 14 - Jul 15
Total with taxes and fees
2nd-floor downtown Ludlow studio condo with kitchenette, streaming
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.
$254 nightly
The price is $287
Jul 20 - Jul 21
Total with taxes and fees
Cozy 3 bedroom condo 2.5 miles to Mount Snow
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
$281 nightly
The price is $317
Aug 4 - Aug 5
Total with taxes and fees
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
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.
$424 nightly
The price is $479
Jul 21 - Jul 22
Total with taxes and fees
Ski-In/Out Condo with Mountain Views, and Washer/Dryer
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
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.
$345 nightly
The price is $378
Aug 12 - Aug 13
Total with taxes and fees
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
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
Jul 14 - Jul 15
Total with taxes and fees
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
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.
$522 nightly
The price is $590
Jul 14 - Jul 15
Total with taxes and fees
Mount Snow Condo: 4 min Walk to Sundance Lift (High Speed - 6 Seat)
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.
$483 nightly
The price is $541
Jul 14 - Jul 15
Total with taxes and fees
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Exterior

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.
$279 nightly
The price is $315
Jul 14 - Jul 15
Total with taxes and fees
Condo in the heart of town near skiing - less than a mile to Okemo Mountain
Interior

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

Ground Floor ski-in/out condo, full kitchen & high-speed WiFi
Clock Tower Base Area
9.4 out of 10, Exceptional, (27 reviews)
"No interaction with host but all amenities were excellent "
United States
Dan M.
$364 nightly
The price is $411
Jul 14 - Jul 15
Total with taxes and fees
Ground Floor ski-in/out condo, full kitchen & high-speed WiFi
Outdoor dining

Okemo | Charming 1BR Condo + Close to Amenities

Okemo | Charming 1BR Condo + Close to Amenities
Jackson Gore Base Area
$272 nightly
The price is $300
Jul 14 - Jul 15
Total with taxes and fees
Okemo | Charming 1BR Condo + Close to Amenities
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
"We had rooms on the first floor, both had a damp and moldy smell. The breakfast was adequate but the warm section ( eggs, sausage, hash brown) doesn’t get replenished often enough and there was always a long wait. Now onto the good part- bathroom was well updated, rooms are clean, parking was easy. Location was good, walkable to town center."
Jia 2-night trip
Posted 9 hours ago
Hotel Vervana, Trademark Collection by Wyndham

Find out more about Bennington

Bennington Condo Rentals information

Number of reviews
473
Accommodation
63 Condo Rentals
Lowest Price
$162
Highest Price
$692

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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