Vacation rentals in Bennington County

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Top-rated vacation rentals in Bennington County

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Cabin in Londonderry

4.93 out of 5 average rating, 308 reviews

Stone Fence Cabin

Cute, Cozy & Charming, our rustic, Studio Cabin is on 5 private acres near scenic Gale Meadows Pond in S Londonderry, VT. We are close to Stratton, Bromley & Manchester and you’ll enjoy beautiful scenery and hiking right outside your front door. The Cabin has an open floor plan with a galley kitchen, dining/living area with pullout futon couch & 1 full bathroom. The sleeping loft is accessible by ladder. Our place is a great fit for couples and solo adventurers looking to get away from it all!

Oct 4 – 11

G$21,834 GYD per night
Guest favorite

Apartment in Bennington

4.94 out of 5 average rating, 154 reviews

NEW Escape the City- Vermont Studio

Our newly renovated studio apartment is located minutes from Bennington College, and sits on 7 acres of land in the Green Mountain National Forest. It's on the second floor of our home through a private entrance with a personal deck and outdoor seating. Take an afternoon to stroll to the Mile Around Woods, or hike to the white rocks! Walk the Ninja trail from the college to see the historic covered bridges, or drive 20-30 miles N to enjoy Vermont's best skiing, and shopping at designer outlets!

Feb 10 – 17

G$19,314 GYD per night
Guest favorite

Apartment in Wilmington

4.88 out of 5 average rating, 277 reviews

Globetrotter Retreat - Minutes to the Mountain

Newly renovated, fully furnished apt in heart of quaint mountain village; minutes to Mount Snow, Green Mountains & lakes. Year round outdoor activities: snow sports in winter, watersports/hiking in summer. Quiet 1 bedroom apt sleeps 4 people in comfort. Private balcony overlooks rolling river. Steps from many restaurants, bars & shopping. Supermarket is a short walk. FreeMoover bus stop across the street - leave your car parked & ride for free to local destinations! No guest under 18 years old.

Aug 14 – 21

G$24,079 GYD per night

Popular amenities for Bennington County vacation rentals

Other great vacation rentals in Bennington County

Guest favorite

Condo in Stratton

4.96 out of 5 average rating, 113 reviews

Cozy condo within walking distance to the slopes.

May 1 – 8

G$27,776 GYD per night
Guest favorite

Apartment in Manchester

4.99 out of 5 average rating, 168 reviews

Style and Comfort- Perfect Year Round Location

Jun 2 – 9

G$30,728 GYD per night
Guest favorite

Apartment in Arlington

4.87 out of 5 average rating, 124 reviews

Brian Peace of Heaven

Mar 20 – 27

G$28,526 GYD per night
Guest favorite

Tiny home in Wilmington

4.98 out of 5 average rating, 128 reviews

Beautiful Timber Frame Retreat

Sep 4 – 11

G$43,783 GYD per night
Guest favorite

Apartment in Wilmington

4.91 out of 5 average rating, 105 reviews

Walk To Wilmington Village (Reduced Spring Rate)

May 17 – 24

G$24,514 GYD per night
Guest favorite

Guesthouse in Pownal

4.84 out of 5 average rating, 479 reviews

Bauhaus Guest House in So. VT.

Jul 30 – Aug 6

G$19,122 GYD per night
Superhost

Cottage in Sunderland

4.88 out of 5 average rating, 152 reviews

Green Mountain Retreat

Apr 12 – 19

G$29,354 GYD per night
Guest favorite

Cottage in Shaftsbury

4.96 out of 5 average rating, 109 reviews

Rollin Cottage

Aug 9 – 16

G$29,354 GYD per night
Guest favorite

Condo in West Dover

4.94 out of 5 average rating, 179 reviews

Comfy Condo - 2 Min Walk to Carinthia Grommet Lift

Dec 12 – 19

G$25,183 GYD per night
Guest favorite

Home in Dover

4.93 out of 5 average rating, 67 reviews

Cozy Riverfront Home, 1mi to Mt Snow, On Moover

May 10 – 17

G$17,801 GYD per night
Guest favorite

Home in Shaftsbury

4.92 out of 5 average rating, 96 reviews

Cheerful 1 bedroom cottage

Sep 27 – Oct 4

G$17,501 GYD per night
Superhost

Cabin in Bennington

4.81 out of 5 average rating, 99 reviews

Vermont Cabin - Secluded Woods on South Stream

Apr 29 – May 6

G$21,860 GYD per night

Destinations to explore