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Check prices for these dates

In two weeks
Feb 27 - Mar 1
In two months
Apr 10 - Apr 12
In three months
May 8 - May 10
In four months
Jun 5 - Jun 7

Our top choices for Bennington condo rentals

Smart TV, fireplace

Luxury Condo Stratton Mountain

Luxury Condo Stratton Mountain
Stratton
10.0 out of 10, Exceptional, (1 review)
"Katherine was a perfect host. The house is beautiful and had everything we needed for our family vacation. Thank you so much! "
United States
Katryn B.
$2,682 nightly
The price is $2,722
Feb 11 - Feb 12
Total with taxes and fees
Luxury Condo Stratton Mountain
Fridge, microwave, oven, stovetop

Stratton Mtn Studio | Renovated | Walk to Lifts

Stratton Mtn Studio | Renovated | Walk to Lifts
Stratton Mountain
10.0 out of 10, Exceptional, (30 reviews)
"Great location."
United States
Jeffrey
$474 nightly
The price is $536
Feb 11 - Feb 12
Total with taxes and fees
Stratton Mtn Studio | Renovated | Walk to Lifts
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
7.4 out of 10, Good, (20 reviews)
"A great weekend. The property was clean and comfortable."
United States
Joan P.
$370 nightly
The price is $419
Mar 10 - Mar 11
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
$585 nightly
The price is $594
Mar 3 - Mar 4
Total with taxes and fees
New! Vermont Getaway! Stratton - close to skiing!
Interior

Ski on ski off condo

Ski on ski off condo
Stratton
9.8 out of 10, Exceptional, (74 reviews)
"Joe was very accommodating with my short notice reservation. Great spot, very spacious! "
United States
Thomas M.
$1,199 nightly
The price is $1,355
Feb 13 - Feb 14
Total with taxes and fees
Ski on ski off condo
Exterior

Chic Condo <1 Mile Away from Stratton’s Village

Chic Condo <1 Mile Away from Stratton’s Village
Stratton
10.0 out of 10, Exceptional, (2 reviews)
"We had a wonderful family getaway at this condo! The hosts did a great job communicating with us, and check-in went smoothly. The place was comfortable and clean, and the location was great—easy access to the mountain via shuttle. We enjoyed our stay very much! "
United States
Miriam P.
$952 nightly
The price is $1,076
Feb 19 - Feb 20
Total with taxes and fees
Chic Condo <1 Mile Away from Stratton’s Village
Exterior

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,233 reviews)
"I great place to stay!!"
United Kingdom
Maricel
$126 nightly
The price is $141
Feb 22 - Feb 23
Total with taxes and fees
Vacation Village in the Berkshires
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, (50 reviews)
"Great quiet location, kitchen had enough essentials for basic cooking to be easy. The king bed was comfortable and the living room is a great hangout spot."
United States
Franklin C.
$267 nightly
The price is $302
Mar 2 - Mar 3
Total with taxes and fees
Cozy 3 bedroom condo 2.5 miles to Mount Snow
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
9.0 out of 10, Wonderful, (77 reviews)
"Perfect location for a quick ski trip. "
United States
Michael D.
$295 nightly
The price is $334
Mar 11 - Mar 12
Total with taxes and fees
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
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, (33 reviews)
"Very nice accommodations and location!"
United States
Michael M.
$323 nightly
The price is $365
Mar 1 - Mar 2
Total with taxes and fees
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
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.
$285 nightly
The price is $322
Feb 11 - Feb 12
Total with taxes and fees
Condo in the heart of town near skiing - less than a mile to Okemo Mountain
Exterior detail

Ski-in/ski-out condo w/ wood-burning fireplace, patio, shared bbq, w/d, wifi

Ski-in/ski-out condo w/ wood-burning fireplace, patio, shared bbq, w/d, wifi
West Dover
$220 nightly
The price is $248
Feb 11 - Feb 12
Total with taxes and fees
Ski-in/ski-out condo w/ wood-burning fireplace, patio, shared bbq, w/d, wifi
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, (23 reviews)
"Great rate for a place with all the basics!"
United States
Macgregor
$254 nightly
The price is $287
Mar 8 - Mar 9
Total with taxes and fees
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Property grounds

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, (28 reviews)
"Overall very clean and nice. Needs some updating like more spoons, only 2, bigger coffee cups. And a new coffee table that is very worn. "
United States
David A.
$305 nightly
The price is $345
Mar 10 - Mar 11
Total with taxes and fees
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
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.
$272 nightly
The price is $307
Feb 24 - Feb 25
Total with taxes and fees
2nd-floor downtown Ludlow studio condo with kitchenette, streaming
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, (103 reviews)
"Ideal location, clean and comfortable condo, and kind, responsive host! The larger bedroom could benefit from blackout curtains, but if you like to wake up to bright sunlight then it's a non-issue!"
United States
Jessica C.
$330 nightly
The price is $361
Mar 3 - Mar 4
Total with taxes and fees
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
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, (21 reviews)
"Amazing place! "
United States
Tara
$473 nightly
The price is $530
Mar 2 - Mar 3
Total with taxes and fees
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Interior

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

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Ludlow
7.4 out of 10, Good, (55 reviews)
"Irish Bar nearby was a plus on St. Patrick’s Day !"
United States
Warren
$319 nightly
The price is $361
Feb 24 - Feb 25
Total with taxes and fees
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
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, (23 reviews)
"Clean room and very comfortable bed. Was ready for check in sooner than expected. "
United States
Wilson V.
$441 nightly
The price is $498
Mar 2 - Mar 3
Total with taxes and fees
Ground Floor ski-in/out condo, full kitchen & high-speed WiFi
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
$1,443 nightly
The price is $1,572
Feb 12 - Feb 13
Total with taxes and fees
Okemo Westwood Condo 3 Bedroom Condo by RedAwning
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

Starlight Inn

Starlight Inn

10/10 Excellent
"Clean "
Michael 1-night trip
Posted 7 days ago
Starlight Inn

Find out more about Bennington

Bennington Condo Rentals information

Number of reviews
2,677
Accommodation
65 Condo Rentals
Lowest Price
$141
Highest Price
$2,722

Frequently asked questions

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How can I find cheap condos in Bennington?
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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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