Holiday Rentals in Old Bennington

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Our top choices for Old Bennington holiday 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 €277
includes taxes & fees
22 Apr - 23 Apr
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 €164
includes taxes & fees
19 Apr - 20 Apr
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 €265
includes taxes & fees
19 Apr - 20 Apr
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

Peaceful getaway at birds of a feather

Peaceful getaway at birds of a feather
Shaftsbury
9.8 out of 10, Exceptional, (32 reviews)
"Great place!!"
United States
Margaret D.
The price is €212
includes taxes & fees
21 Apr - 22 Apr
Peaceful getaway at birds of a feather

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 €290
includes taxes & fees
19 Apr - 20 Apr
Florida Mountain Log Cabin

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 €265
includes taxes & fees
19 Apr - 20 Apr
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

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 €250
includes taxes & fees
22 Apr - 23 Apr
Cozy 3 bedroom condo 2.5 miles to Mount Snow

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 €241
includes taxes & fees
22 Apr - 23 Apr
2-Bdr Apt In Town, By the Water

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 €129
includes taxes & fees
19 Apr - 20 Apr
Getaway Near Mass MoCA, Great Hiking, Scenic Views

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 €263
includes taxes & fees
22 Apr - 23 Apr
NEW Ski in/out condo with Mt views, hot tub, porch, gym & wifi!

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
9.6 out of 10, Exceptional, (26 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 €380
includes taxes & fees
27 Apr - 28 Apr
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

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.
Downtown | Waterfront | Walk to Shops

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 €374
includes taxes & fees
20 Apr - 21 Apr
North Getaway Cottage

Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (2 reviews)
"This home is super cozy and had all the amenities I needed after a long drive. I will be staying here again."
United States
Jess M.
The price is €164
includes taxes & fees
19 Apr - 20 Apr
Cozy Home in Pownal VT

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 €230
includes taxes & fees
20 Apr - 21 Apr
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 €352
includes taxes & fees
20 Apr - 21 Apr
Modern Mount Snow Gnarvana - Walk to Lodge & Lifts, Balcony, Loft

Deluxe Studio | Murphy Bed + Sofa

Deluxe Studio | Murphy Bed + Sofa
West Dover
The price is €181
includes taxes & fees
20 Apr - 21 Apr
Deluxe Studio | Murphy Bed + Sofa

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 €195
includes taxes & fees
20 Apr - 21 Apr
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 €252
includes taxes & fees
19 Apr - 20 Apr
Brookside cottage near the mountains and outdoor recreation

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 €208
includes taxes & fees
28 Apr - 29 Apr
Spacious apartment in beautiful, historic Arlington VT
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

Everything you need to know about Old Bennington holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Old Bennington holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Old Bennington holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Old Bennington holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Old Bennington. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Old Bennington holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Old Bennington holiday rentals we have selected for you start as low as €208 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Old Bennington rentals

At Expedia, we put the best Old Bennington holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Old Bennington rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Old Bennington holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Old Bennington. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Old Bennington?

Yes, there are holiday rentals close to the most popular sights in Old Bennington, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Old Bennington has to offer?

Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating : This holiday home rental outside of Old Bennington is located on a lake, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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

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

What’s a holiday rental in Old Bennington like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Old Bennington. Holiday rentals feature extras such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a clean environment, a holiday rental can provide a sense of privacy away from public hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for families.