Hotel vacation rentals in Bennington County

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Top-rated hotel rentals in Bennington County

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Superhost

Hotel in Wilmington

5.0 out of 5 average rating, 5 reviews

Brook Bound Inn-Main Lodge-King Room 201-2nd Floor

Now Under New Ownership! Just down the road from Dover Vermont and the historic town of Wilmington Vermont, the Brook Bound Inn is 32 acres located along the Cold Brook Stream. The Inn consists of the Main Lodge, Rustic Cabin, and Carriage House. Our accommodations include a number of large rooms and suites. Located minutes from Downtown Dover, the Hermitage Ski resort, Haystack Golf club, and Mt. Snow ski resort. The property offers a pool, sports court, outdoor fire pit, and propane grilles.

Apr 5 – 12

G$55,398 GYD per night

Superhost

Boutique hotel in Dover

5.0 out of 5 average rating, 7 reviews

Luxury King Suite w/balcony in Historic Inn, rm 1

Deluxe King Suite with balcony and living room inside of our newly renovated historic Inn. King bed and a queen pullout sofa. This unit has 1 full bath with double sinks and 1 half bath. Room comes with towels, toilet paper, shampoo, conditioner, body lotion and other toiletries. The expansive balcony has a bistro set for enjoying a coffee or happy hour. This unit also has a mini fridge and Keurig coffee maker. We provide K-cups, tea, sugars and various snacks. Inn room 1 is not pet friendly.

Jul 2 – 9

G$60,272 GYD per night

Superhost

Hotel in Wilmington

4.75 out of 5 average rating, 4 reviews

Brook Bound Inn-Main Lodge-Two Bedroom Suite 102

Sep 4 – 11

G$86,786 GYD per night

Boutique hotel in Winhall

5.0 out of 5 average rating, 3 reviews

Bromley View Inn Suite #8

Welcome to the Bromley View Inn, where strangers become friends. While staying in this suite you will have access to our large lounge featuring a fire place, tons of seating, a bar and work table. Outdoors guests will have access to our beautiful deck with fire pits and seating looking over Bromley Mountain. Around the grounds you'll find two ponds, a scenic and walkable property with plenty of space to enjoy. We are 4 miles from Bromley Mountain and just 7 from both Manchester and Stratton.

Feb 18 – 25

G$32,488 GYD per night

Guest favorite

Boutique hotel in Bennington

4.97 out of 5 average rating, 29 reviews

Harwood Hill Motel - Farmhouse Suite Down

Our downstairs Farmhouse Suite combines elegance and whimsy. This private, two-bedroom suite has one queen bedroom, a second twin bedroom, a spacious living room with a pull-out queen sofabed, and a full-size kitchen and bath. In addition to the unique artwork and custom design features throughout, the suite has its own private porch. The farmhouse is on the grounds of a small, boutique motel with a large lawn, a gazebo, picnic tables, fire ring, and grill that our guests are welcome to use.

Jul 7 – 14

G$65,992 GYD per night

Guest favorite

Boutique hotel in Bennington

5.0 out of 5 average rating, 13 reviews

Harwood Hill Motel - Deluxe Two Queens

Set into the hillside surrounded by an apple orchard on one side and mountains on the other, The Harwood Hill offers respite in the Southern Vermont countryside within a 10-minute drive to Bennington's restaurants, galleries, and museums. Our rooms are modern and fully renovated, with local art inside and out. Relax around the corner on our great lawn, with a hammock, picnic tables, fire ring, and a splendid view of Mount Anthony. On weekends, we provide complimentary continental breakfast.

May 2 – 9

G$39,969 GYD per night

Guest favorite

Boutique hotel in Bennington

4.94 out of 5 average rating, 51 reviews

Harwood Hill Motel - Deluxe Queen

Aug 7 – 14

G$39,119 GYD per night

Guest favorite

Hotel in Whitingham

4.94 out of 5 average rating, 170 reviews

The Engel House Room 3: Mt Snow/Wilmington VT Area

Escape to Vermont in this historical house located near Mount Snow, Wilmington, Brattleboro and Bennington. In Spring and Summer enjoy Harriman Reservoir or take in local historical sights, in Fall admire the breathtaking foliage, and in Winter ski Mount Snow or Stratton Mountain. And along with your private room and connected private bathroom are several guest common areas (not part of the hosts' living area). Our charming old house will perfect your trip to the green mountains of Vermont.

Jun 22 – 29

G$31,253 GYD per night

Guest favorite

Boutique hotel in Bennington

4.9 out of 5 average rating, 67 reviews

Harwood Hill Motel - Cottages Queen+Twin Sofabed

Set into the hillside surrounded by an apple orchard on one side and mountains on the other, The Harwood Hill offers respite in the Southern Vermont countryside within a 10-minute drive to Bennington's restaurants, galleries, and museums. Our rooms are quaint and comfortable, with local art inside and out. Relax on our great lawn, with a hammock, picnic tables, fire ring, and a splendid view of Mount Anthony. On weekends, we provide complimentary continental breakfast.

Aug 26 – Sep 2

G$40,309 GYD per night

Boutique hotel in Manchester

New place to stay

Luxurious Room Incl Pool & Hot Tub Access and More

Uncover the enduring charm of Charles Orvis Inn, an historic 19th-century treasure nestled beside the Main Inn, mere moments from the resort's array of activities and facilities. Immerse yourself in a quintessential Vermont escape, complete with a snug library, a fireside lounge, modern amenities like air-conditioning and electric car charging, and a picturesque New England porch. Embark on a journey to serenity and heritage at this tranquil retreat!

Apr 18 – 25

G$150,931 GYD per night

Hotel in Shaftsbury

4.67 out of 5 average rating, 3 reviews

Dog friendly Queen Room

You won’t want to leave this charming, one-of-a-kind place. Beautifully located in the Village of Shaftsbury, in Southwestern Vermont’s expansive Green Mountain region. Our motel offers a serene and quiet rural setting with impressive mountain views. This room is dog-friendly with hardwood floors. Relax on the queen bed, or enjoy your own private microwave, refrigerator, and coffee maker.

Nov 18 – 25

G$41,731 GYD per night

Hotel in Wilmington

4.91 out of 5 average rating, 11 reviews

Standard Queen

Fitted with a Queen bed, our standard rooms are perfectly suited for two guests seeking a relaxing mountain getaway. Each room has a private bath and all traveling necessities, including wifi. Full of natural light, the windows in each room offer idyllic views while curated furnishings and quality linens invite you to relax.

Sep 13 – 20

G$49,422 GYD per night