Holiday rentals in Bennington County

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Top-rated holiday rentals in Bennington County

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Guest favourite

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!

21–28 Aug

$142 SGD per night

Guest favourite

Cabin in Jamaica

4.99 out of 5 average rating, 184 reviews

New Cabin in Jamaica

Recently constructed 500sq ft passive solar cabin, 10 minutes to Stratton Mtn., 20 minutes to Mt. Snow and Dover for skiing, shopping, food, or a beer at Snow Republic. Quiet road but very accessible. Perfect area for hiking, biking, relaxing walks along the Ball Mountain Brook or kayaking on Grout Pond or Gale Meadows. Enjoy a campfire in the side yard/former pony corral or relax on the spacious screened in porch. 30 minutes from seasonal farmers market and from Manchester for outlets.

10–17 Sep

$206 SGD per night

Guest favourite

Chalet in Dover

4.93 out of 5 average rating, 264 reviews

A charming VT chalet

Charming chalet nestled in the Mt Snow valley. Relax to the sound of a babbling brook in the back yard while you hang around a stone fire pit! Unwind in the quiet serenity of this country home complete with fully equipped kitchen with a newly installed gas fireplace , a comfy open living room with flat screen cable tv & DVD player Roko & High speed Internet . We have a lock box located on the post near the front entrance. combo provided upon arrival . Washer & dryer located on first level.

12–19 Mar

$224 SGD per night

Guest favourite

Flat in Manchester

4.99 out of 5 average rating, 145 reviews

Private two-bedroom suite within a two-story house

This is a private suite located on the second floor of a house. Separate entrance. The owners live downstairs. Great location with mountain views. Please note: 1) Our kitchen is fully equipped, but it has a hot plate instead of the traditional stove. 2) Instead of a full-size living room there is a small sitting area with a TV in the same area where the kitchen is located. 3) Guests don't have access to the backyard/patio, but you can enjoy the outside seating set in front of the house.

27 Apr – 4 May

$108 SGD per night

Superhost

Cabin in Wardsboro

4.8 out of 5 average rating, 202 reviews

Log Cabin Near Stratton/Mt Snow

Rustic log cabin for those looking for a getaway and a real Vermont experience. Pets allowed with *PET FEE* - add to your reservation There is Wifi &cell service (AT&T, Verizon). Please be aware this is not a luxury cabin, it is an authentic log cabin that we enjoy as a family during all seasons. No cable television - there is a TV with a Chromecast that you can use to stream from your phone over wifi. Firewood not provided 20 minutes to Stratton and 15 minutes to Mt. Snow

15–22 May

$135 SGD per night

Guest favourite

Guest house in North Bennington

4.98 out of 5 average rating, 150 reviews

Birch House - lake, green trees + modern comforts

We're a little guest house near a lake in Vermont with green trees + modern comforts. Perfect for couples + individuals looking to relax + enjoy nature. Renovated, air conditioned light space with cozy, minimalist vibes. A small modern cabin that's peaceful + private. Tucked into a quiet neighborhood. Main home is a separate building next door. Near Bennington College. 12 minutes to downtown Bennington. Please note that due to a severe allergy, we cannot accommodate animals.

17–24 Oct

$213 SGD per night

Guest favourite

Cottage in Shaftsbury

4.99 out of 5 average rating, 597 reviews

Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub

This newly-renovated historic schoolhouse overlooks our family's regenerative organic farm. The Schoolhouse is bright & open, with a modern design & peaceful, rustic feel. It is the perfect place to relax & enjoy a country setting with views of the Green Mountains in every direction. We have added a new private deck at the Schoolhouse property, with a hot tub & panoramic barrel sauna. Come to unwind, cook, & enjoy a quintessential Vermont experience on our 350 acre property.

19–26 Feb

$591 SGD per night

Superhost

Cabin in Shaftsbury

4.9 out of 5 average rating, 381 reviews

The LoveNest -Charming private cabin on 65 acres

The Love Nest has returned! We’re high up on the hill yet close to art and culture, great views, restaurants and dining, family-friendly activities, skiing, Bennington, Manchester VT close by. Williamstown Mass not far. A huge yard. You’ll love my place because of the coziness, the light, the comfy bed, the well equipped kitchen, privacy and views, the extreme quiet and relaxation. Waterfalls! My place is good for couples, solo adventurers, and dog guests. 420 friendly!

17–24 May

$184 SGD per night

Superhost

Cottage in Sunderland

4.88 out of 5 average rating, 152 reviews

Green Mountain Retreat

This is a modern three bedroom, two bath in one of the most beautiful places in New England - nestled in the Green Mountain National Forest, across the road from the Roaring Branch River. About 12 minutes from Manchester and 20 minutes from Bennington. It is close to all of the best trails in Southern Vermont, several beautiful mountain lakes, and Stratton and Bromley ski resorts. If you enjoy outdoor activities, this is the most ideal location in Southern Vermont.

25 Apr – 2 May

$191 SGD per night

Guest favourite

Flat in Bennington

4.96 out of 5 average rating, 139 reviews

Cooper's Place

Small bright and cozy apartment nestled in the Shires of Vermont. A mid-modern space with VT flare and all of the amenities you need to enjoy your getaway. Housed behind a unique building that was once a manufacturer of concrete blocks and is still a hardscape retail store located in downtown Bennington called Morse Brick & Block. Enjoy the porch or have a fire in the fire pit. Take a trip to the Bennington Monument and Museum. Close to hiking trails and ski areas.

4–11 Jun

$136 SGD per night

Guest favourite

Flat in Arlington

4.87 out of 5 average rating, 127 reviews

Brian Peace of Heaven

Beautiful Mountain View 4 1/2 Acres Park your vehicle inside garage upstairs studio apt with full kitchen and Bathroom with shower. There 100 acres to the right and 40 to the left. welcome to Brian’s peace of Heaven.. There skiing 10miles a way Stratton and Bromley. Out let’s Stores in Manchester Vt . Roads are always plowed in winter. Pellet stove that you can use with Gas heat and hot water. 2 beds queen size and Full size.

17–24 Sep

$186 SGD per night

Guest favourite

Flat in Bennington

4.91 out of 5 average rating, 163 reviews

Scenic Vermont Studio

This beautiful retreat is halfway between the ski slopes of southern Vermont and the cultural centers of Williamstown and North Adams, MA. The residence is a modern, spacious, basement apartment, part of an 1860 farm house. It has its own private entrance around the back of the house at ground level. Solar garden lights and motion detector lighting will illuminate your path to the apartment.

17–24 Aug

$137 SGD per night