Vacation rentals in Shaftsbury

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Top-rated vacation rentals in Shaftsbury

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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 17 – 24

€ 101 per night

Guest favorite

Cabin in Shaftsbury

4.99 out of 5 average rating, 200 reviews

The Hygge Loft- mid-mod cabin on 70 forested acres

The Hygge Loft: a midcentury modern-designed cabin nestled among 70 acres of privately-owned forest with rivers & hiking trails. Enjoy sipping an espresso or wine while listening to vinyl records, cozied up by the wood-burning fireplace. Take a walk in the forest to the river or stargaze by the firepit on the private deck. Indulge in a luxurious bath or snuggle up in the ultra comfy king-size bed with views of treetops and sky all around. It’s the kind of place you’ll never want to leave!

Jan 10 – 17

€ 369 per night

Guest favorite

Cabin in Shaftsbury

5.0 out of 5 average rating, 108 reviews

Renovated Log Cabin Lodge-EV & Pets-Hike-Hot Tub

Reunite with nature at the newly renovated log cabin Lodge at Taconic Ridge. Hundreds of acres of Taconic mountain wilderness and hiking are accessible from the backyard of this home located as the last house on a quiet dead-end road. Fresh, clean, spacious, and open concept, the lodge has all of the amenities that we enjoy most when traveling, and pet friendly too. Head out to explore all that the southern Vermont tri-state area has to offer, or bring groceries and never have to go out!

Aug 30 – Sep 6

€ 549 per night

Guest favorite

Home in Shaftsbury

4.84 out of 5 average rating, 105 reviews

Quaint One-Story Vermont House with Mountain View

From our quaint one-story house, you can see a variety of scenery, from the bright changing colors of the leaves in the autumn to the soft piles of snow in the winter. Experience the quiet of the nearby woods, and see roaming animals such as deer or turkey. Make sure to stop at one of the nearby lakes, each of which offers a variety of amenities, and lush scenery. In the winter, keep warm in the cozy living room next to the fireplace, while having a chat with your friends and family.

Apr 24 – May 1

€ 217 per night

Superhost

Home in Bennington

4.85 out of 5 average rating, 153 reviews

Bennington Guest Barn 3 Bedrooms

Really sweet 3 complete bedrooms with 1 rollout bed. New & decorated in typical Vermont decor. Many amenities provided to make your stay feel like home. Convenient location: 1 mile to Bennington College, 20 miles to Mass MOCA, Mt. Snow, Jiminy Peak and Bromley are within 30 miles and 8 miles to Cross Country Ski at Prospect Mt. Robert Frost, Bennington Museums along with three unique Covered Bridges are 1 – 3 miles away. Find out why people love Vermont and keep coming back.

Apr 24 – May 1

€ 150 per night

Guest favorite

Guesthouse 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.

Oct 8 – 15

€ 178 per night

Guest favorite

Cottage in Shaftsbury

4.99 out of 5 average rating, 596 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.

Nov 12 – 19

€ 459 per night

Guest favorite

Guest suite in Shaftsbury

4.98 out of 5 average rating, 131 reviews

Country Getaway with a Spa/Birds of a Feather Farm

Our cozy upstairs studio can accommodates up to 4 and is separate from the main house. Plush towels, linen, pillows and blankets. Kitchenette is fully stocked with everything you need for cooking. The private entrance is equipped with punch key lock to facilitate easy self check-in. A queen size sleep number bed, queen size pullout couch, table with four chairs, a dresser, one bathroom with shower, smart TV and WIFI. Heat and cooling. A spa is available and infrared sauna.

Aug 25 – Sep 1

€ 138 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!

Aug 20 – 27

€ 180 per night

Guest favorite