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Bennington College, Bennington, North Bennington, Vermont, United States of America

Bennington College vacation rentals

We found 421 vacation rentals — enter your dates for availability

Discover a selection of 421 vacation rentals in Bennington College, Bennington that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $73 per night, and condos and cabins are popular options for a stay in Bennington College. Either way, you'll find a rental for everyone's needs.
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Find spaces that suit your style

Condos/Apartments

View 73 Condos/Apartments

Cabins

View 31 Cabins

Houses

View 292 Houses

Cottages

View 31 Cottages

Chalets

View 18 Chalets

Bungalows

View 31 Bungalows

Townhouses

View 48 Townhouses

Studios

View 24 Studios

Find the best place to stay — Bennington College

Romantic Private Vermont Cottage, dogs welcome

Sleeps 4 · 1 Bedroom · 1 Bathroom
$185 avg/night
(121)

Cozy Converted Barn on Secluded 6.5 acres

Sleeps 8 · 1 Bedroom · 1 Bathroom
$128 avg/night
(120)

Cozy 1 Bedroom farm stay cottage

Sleeps 4 · 1 Bedroom · 1 Bathroom
$86 avg/night
(1)

Studio style farm stay

Sleeps 2 · 1 Bedroom · 1 Bathroom
$73 avg/night
(4)

Bennington Guest Farmhouse

Sleeps 9 · 5 Bedrooms · 2 Bathrooms
$200 avg/night
(15)

Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill

Sleeps 4 · 2 Bedrooms · 1 Bathroom
$162 avg/night
(10)

Search 421 vacation rentals

Top rated rentals — Bennington College
Stayed Jan 2021

Great Ski Week

Great week. Property was clean and spacious - listing was accurate and exactly what we expected. The basement game room was a hit with teens and adults alike. Joe was a great host and even helped us by contacting the HOA to re-sand the driveway when ...

Ryan M.
Ryan M.
Stayed Jan 2021

Perfect

This cabin was the PERFECT place to hideaway. The house is just remote enough to feel like you are all alone, but close enough to a wonderful market down the street that it is convenient. The cabin itself is incredibly creatively constructed and so c...

Kate L.
Kate L.
Stayed Jan 2021

Wonderful home

After our 5 hour long drive, the much needed “perfect home” was long overdue. This home checked off every box. A well lit shoveled driveway welcomed us. The house was clean, accommodating, and very cozy. Our kids loved the hot tub. We skied Bromley a...

Chris V.
Chris V.
Stayed Dec 2020

Beautiful house and property

We had a wonderful, relaxing stay at Pleasant Valley. The house is spacious and comfortable - love the seating area on the second floor - and the fireplace made everything cozy each night. A few of us had a great time exploring the fields behind the ...

Megan G.
Megan G.
Stayed Nov 2020

Perfect Getaway

Catamount Cottage is a charming property across the street from a whitewater brook. The cottage is well-stocked and in a beautiful location to go walking. The furnishings were great and there are lots of great hiking trails in the area. We will defin...

Megan E.
Megan E.
Stayed Nov 2020

Just what the doctor ordered

We came for rest and relaxation by a fire, and that's what we got. The place was simple and perfect. Great spot on the mountain. Perfect for hikers, as it's close to a really nice trailhead. Host was helpful and responsive. No complaints. Would defin...

Eli C.
Eli C.

Philadelphia

Stayed Nov 2020

Great Getaway

We really enjoyed our stay. It was just what we were looking for after a crazy year of planning and re-planning our wedding. We were able to escape for a secluded honeymoon filled with hikes and a warm fire. The chalet was very well-kept, and we felt...

Nicolas D.
Nicolas D.
Stayed Nov 2020

Amazing weekend getaway!

Spent a long weekend here with my boyfriend and my dog and it couldn't have been more perfect! The cottage had everything we needed and the surrounding area was beautiful. Lots of great hiking in the area and a very cute little downtown. We hope to c...

Kathleen S.
Kathleen S.
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How many vacation rentals are available around Bennington College, Bennington?

Our 2021 property listings offer a large selection of 421 vacation rentals around Bennington College. From 73 condo and apartment rentals to 31 cabin rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent Condos/Apartments near Bennington College?

Yes, of course. Vrbo has 73 Condos/Apartments near Bennington College. Our other popular types of vacation rentals near Bennington College include:

  • Cabins: 31 rentals available
  • Houses: 292 rentals available
  • Cottages: 31 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Chalets and more.

Can I find a vacation rental with pool near Bennington College?

Yes, you can select your preferred vacation rental with pool among our 129 vacation rentals with pool available near Bennington College. Please use our search bar to access the selection of vacation rentals available.

    Can I book a vacation rental directly online or instantly near Bennington College?

    Yes, Vrbo offers a selection of 421 vacation rentals to book directly online and 208 with instant booking available near Bennington College. Don't wait, have a look at our vacation rentals via our search bar and be ready for your next trip near Bennington College!