Boutique hotel holiday rentals in Bennington County

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Top-Rated Boutique Hotels in Bennington County

Guests agree: These boutique hotel rentals are highly rated for location, cleanliness and more.

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Superhost

Hotel room in Dover

5 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.

Guest favourite

Hotel room in Bennington

5 out of 5 average rating, 18 reviews

Harwood Hill Motel - Deluxe King

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.

Guest favourite

Hotel room in Bennington

5 out of 5 average rating, 14 reviews

Harwood Hill Motel - Deluxe Two Queens

Guest favourite

Hotel room in Bennington

4.92 out of 5 average rating, 52 reviews

Harwood Hill Motel - Deluxe Queen

Top Guest favourite

Hotel room in Bennington

4.97 out of 5 average rating, 34 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.

Hotel room in Winhall

4.6 out of 5 average rating, 5 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.

Superhost

Hotel room in Bennington

5 out of 5 average rating, 15 reviews

Harwood Hill Motel - Economy Full plus Single

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.

Hotel room in Dover

Ski-In Mountain Suite | Cozy Escape

Wake up to the beauty of Mount Snow in this charming 1 Bedroom Suite at Grand Summit Resort. Enjoy slopeside convenience with ski-in/ski-out access and unwind in cozy Vermont-inspired comfort. Whether in a loft-style layout or a private-bedroom setup, you’ll have a comfy king or queen bed, a pull-out sofa, and a fully equipped kitchenette. After an adventure-filled day, relax in the heated outdoor pool, hot tubs, or the full-service spa.

Hotel room in Manchester

Elevated Escape | Cupola Suite + Local Favorites

Immerse yourself in the heart of Equinox Resort's luxuries and charm, where every detail speaks to the resort's history of elegance. From grand architecture to refined interiors, enjoy spacious accommodations, world-class amenities, and the quintessential New England ambiance. In the resort's main area, this bi-level suite offers you plenty of room to relax, ideal for groups of up to 4.

Hotel room in Dover

Mount Snow Boutique Hotel - Two Bedroom Gardenview

Family-Friendly 2BR Suite – Comfort & Privacy 🛏️ Sleeping – 2 bedrooms, 2 bathrooms – 1 queen or king bed – 1 twin bunk bed 🌿 Ambiance – Calming atmosphere – Elegant décor throughout – Ideal for families or small groups ✨ Experience – Private, relaxing space for everyone – Designed for comfort, peace, and connection Make memories in a serene family retreat.

Hotel room in Dover

Mount Snow Boutique Hotel - Mountain Suite

⛰️ Spacious King Suite – Views, Comfort & Elegance 🛏️ Sleeping – 1 bedroom with a plush king bed 🔥 Comforts – Cozy fireplace – Inviting seating area – Dedicated work desk 🌄 Ambiance – Sweeping mountain views – Thoughtfully curated décor – Elegant, serene atmosphere Perfect for peaceful mornings, relaxing evenings, and an unforgettable stay.

Hotel room in Dover

4.35 out of 5 average rating, 34 reviews

Standard Two Double at Boutique Hotel in Vermont

For friends or family, our Standard Two Double Bed rooms with one full bathroom offer extra space and comfort. Our recent updates, including sound-deadening between rooms and energy efficient A/C & heating ensure you’ll wake rested and refreshed. Take in the views from your balcony or meadow-view windows and let nature beckon you outdoors.