Old Bennington Vacation Rentals

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Our top choices for Old Bennington vacation rentals

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Dover
9.4 out of 10, Exceptional, (23 reviews)
"Perfect spot for Mount Snow "
United States
Bobby
The price is CA $85
CA $437 total
includes taxes & fees
Apr 13 - Apr 14
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

Peaceful Cottage Retreat

Peaceful Cottage Retreat
cambridge
9.8 out of 10, Exceptional, (47 reviews)
"Perfect little stay. Best parts of being out in the middle of the woods that also has great cell service. Everything you'd need to enjoy a couple days out in "
United States
Victor L.
The price is CA $173
CA $261 total
includes taxes & fees
Apr 13 - Apr 14
Peaceful Cottage Retreat

Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
Hoosick Falls
9.8 out of 10, Exceptional, (103 reviews)
"The host was very responsive and helpful. The property itself was also fantastic, with plenty of amenities and kept very clean."
United States
Jon
The price is CA $161
CA $429 total
includes taxes & fees
Apr 13 - Apr 14
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

Peaceful Stay at Birds of a Feather Farm & Spa

Peaceful Stay at Birds of a Feather Farm & Spa
Shaftsbury
9.8 out of 10, Exceptional, (32 reviews)
"Great place!!"
United States
Margaret D.
The price is CA $137
CA $341 total
includes taxes & fees
Apr 13 - Apr 14
Peaceful Stay at Birds of a Feather Farm & Spa

Florida Mountain Log Cabin

Florida Mountain Log Cabin
Florida
10.0 out of 10, Exceptional, (4 reviews)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
The price is CA $254
CA $472 total
includes taxes & fees
Apr 13 - Apr 14
Florida Mountain Log Cabin

North Getaway Cottage

North Getaway Cottage
Williamstown
9.2 out of 10, Wonderful, (24 reviews)
"We stayed here on a beautiful fall weekend so that my son could tour William's college. It was perfect!"
United States
Carole S.
The price is CA $280
CA $621 total
includes taxes & fees
Apr 13 - Apr 14
North Getaway Cottage

NEW Ski in/out condo with Mt views, hot tub, porch, gym & wifi!

NEW Ski in/out condo with Mt views, hot tub, porch, gym & wifi!
Dover
9.4 out of 10, Exceptional, (9 reviews)
"rented for a ski trip, was nice clean and accommodating. "
United States
yehuda t.
The price is CA $123
CA $421 total
includes taxes & fees
Apr 14 - Apr 15
NEW Ski in/out condo with Mt views, hot tub, porch, gym & wifi!

Getaway Near Mass MoCA, Great Hiking, Scenic Views

Getaway Near Mass MoCA, Great Hiking, Scenic Views
Stamford
9.8 out of 10, Exceptional, (30 reviews)
"We enjoyed our stay "
United States
Lydia T.
The price is CA $93
CA $198 total
includes taxes & fees
Apr 13 - Apr 14
Getaway Near Mass MoCA, Great Hiking, Scenic Views

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, (51 reviews)
"Great cozy apartment right next to a ski resort"
United States
Mikhail S.
The price is CA $125
CA $410 total
includes taxes & fees
Apr 20 - Apr 21
Cozy 3 bedroom condo 2.5 miles to Mount Snow

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
8.8 out of 10, Excellent, (36 reviews)
"Great place with great amenities! "
United States
Rachel R.
The price is CA $98
CA $427 total
includes taxes & fees
Apr 13 - Apr 14
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

New Studio In Town, By the Water

New Studio In Town, By the Water
Williamstown
10.0 out of 10, Exceptional, (10 reviews)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
The price is CA $166
CA $370 total
includes taxes & fees
Apr 13 - Apr 14
New Studio In Town, By the Water

Modern Mount Snow Gnarvana - Walk to Lodge & Lifts, Balcony, Loft

Modern Mount Snow Gnarvana - Walk to Lodge & Lifts, Balcony, Loft
Dover
10.0 out of 10, Exceptional, (26 reviews)
"Great location, clean. Easy to walk to magic carpet."
United States
Anonymous traveller
The price is CA $181
CA $589 total
includes taxes & fees
Apr 15 - Apr 16
Modern Mount Snow Gnarvana - Walk to Lodge & Lifts, Balcony, Loft

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Dover
9.8 out of 10, Exceptional, (25 reviews)
"Decently-sized rooms, great lighting, plenty of space for families with kids to relax, enjoy the outdoor space, easy drive to Stratton and Wilmington. "
United States
SZU YIN C.
The price is CA $147
CA $607 total
includes taxes & fees
Apr 13 - Apr 14
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

Spacious apartment in beautiful, historic Arlington VT

Spacious apartment in beautiful, historic Arlington VT
Arlington
10.0 out of 10, Exceptional, (61 reviews)
"Love staying here! Kate is so friendly, and the place is the perfect spot to rest and recover after ski days. Spacious kitchen allows us to cook and enjoy our own meals. We will book again!"
United States
Eric W.
The price is CA $237
CA $335 total
includes taxes & fees
Apr 13 - Apr 14
Spacious apartment in beautiful, historic Arlington VT

Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn

Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn
Dover
9.6 out of 10, Exceptional, (5 reviews)
"Amazing experience at Mount Snow! Leah is the best owner! Attentive and accessible. "
United States
Jayanne S.
The price is CA $171
CA $577 total
includes taxes & fees
Apr 13 - Apr 14
Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn

Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops
Williamstown
10.0 out of 10, Exceptional, (7 reviews)
"Perfect setup for anyone visiting Williamstown."
United States
Michael P.
The price is CA $180
CA $399 total
includes taxes & fees
Apr 26 - Apr 27
Downtown | Waterfront | Walk to Shops

Deluxe Studio | Murphy Bed + Sofa

Deluxe Studio | Murphy Bed + Sofa
West Dover
The price is CA $230
CA $287 total
includes taxes & fees
Apr 21 - Apr 22
Deluxe Studio | Murphy Bed + Sofa

2-Bdr Apt In Town, By the Water

2-Bdr Apt In Town, By the Water
Williamstown
9.6 out of 10, Exceptional, (12 reviews)
"wonderful apartment right in town."
United States
Stuart S.
The price is CA $166
CA $388 total
includes taxes & fees
Apr 17 - Apr 18
2-Bdr Apt In Town, By the Water

Ski-In Resort Room | 2 Queen Beds

Ski-In Resort Room | 2 Queen Beds
West Dover
10.0 out of 10, Exceptional, (1 review)
"Such a fun location with wonderful staff!"
United States
Christianna R.
The price is CA $251
CA $313 total
includes taxes & fees
Apr 20 - Apr 21
Ski-In Resort Room | 2 Queen Beds

Brookside cottage near the mountains and outdoor recreation

Brookside cottage near the mountains and outdoor recreation
Readsboro
10.0 out of 10, Exceptional, (1 review)
"This place is simply fantastic. If you are looking for quiet...and I mean ABSOLUTE quiet...this is your place! Nestled just five minutes south of Readsboro, VT, Brookside Cottage is the place to get disconnected and just breathe a bit. Our family needed this place...I needed to be here...with our kids growing up so fast, now at 14 and 11, my wife and I just wanted to have a few days to be together, play some games, watch some movies, and enjoy each other's company. I'm convinced we found the...
United States
Jason H.
The price is CA $249
CA $405 total
includes taxes & fees
Apr 14 - Apr 15
Brookside cottage near the mountains and outdoor recreation
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 Old Bennington Hotel Reviews

Find out more about Old Bennington

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Old Bennington. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a vacation rental in Old Bennington?

Yes, you can find vacation rentals near the most popular points of interest in Old Bennington, or you can choose a more remote option if you're looking for relaxation.

What are some of the best vacation home rentals in Old Bennington?

Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating : This vacation home rental outside of Old Bennington is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

What’s there to see and do in Old Bennington?

Explore the area and cultural attractions such as Bennington Museum, or visit a family-friendly sight such as Sugar Shack. Other places in town to visit include Bennington Battle Monument and Old First Congregational Church.

What’s a vacation rental in Old Bennington like?

Vacation rentals are private properties you can stay in for a few weeks or just a few days in Old Bennington. Vacation rentals feature extras such as hot tubs, fire pits, and patios so you'll feel just like you're at home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and busy reception areas while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for family trips or small group gatherings.