Bed and breakfast vacation rentals in Bennington County

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Top-rated bed and breakfast rentals in Bennington County

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Guest favorite

Room in Bennington

4.93 out of 5 average rating, 71 reviews

E & E’s B & B King Bed Rm Bed and Breakfast

Large Private Room with King Size bed also capable of adding an extra single bed to room for extra fee 2 yrs,& older.Room sits behind a large lounge area that leads outside to the hot tub (open year round) and outdoor in-ground pool (seasonal). You have a vanity/Laptop/ phone plug in workspace in room and in lounge. Dorm Refrigerator in room Partial closet use Large dresser Extra storage for personal products and items. Free Laundry Room Use (limited loads.) Free Breakfast (Seas) patio Dining

Jul 23 – 30

G$23,513 GYD per night

Guest favorite

Home in Wilmington

4.97 out of 5 average rating, 34 reviews

Find your escape at The Coldbrook House, Mt Snow

A beautifully-secluded modern ski home near Mt Snow with 500 feet of private access to the Cold Brook. Exceptionally furnished with custom wood flooring and stone fireplace, Subzero & Wolf appliances, walk-in shower with custom river rock flooring, pool table, shuffleboard, and 7-person hot tub. 10 min to Mount Snow, 30 to Stratton. 5 min to downtown Wilmington and Herriman Reservoir. Perfect for 3-4 families or couples trips. Come enjoy the beauty of Southern Vermont at The Coldbrook House!

Jul 29 – Aug 5

G$223,466 GYD per night

Guest favorite

Cabin in Wilmington

5.0 out of 5 average rating, 56 reviews

Modern Chalet-private deck/firepit/ clubhouse pool

Nestled in the Green Mountains this custom modern chalet is the perfect location for your family vacation! Enjoy the peaceful tranquility, 12 min. from Mt Snow. The private wrap around deck is the place to be for morning sunrise & coffee Located in Chimney Hill, includes outdoor & indoor pool, gym, tennis, basketball cts. Harriman Reservoir & Lake Raponda for kayaking/ swimming & Wilmington restaurants & shopping are close by. The home is pet free & has high speed fiber! Insta @bearlairlodge

Feb 10 – 17

G$170,740 GYD per night

Cabin in Peru

5.0 out of 5 average rating, 8 reviews

Renovated new rental. Clean & comfy family home.

Our family friendly home is located in a desirable location, situated on a private road and beautiful setting. Peru, VT is minutes to Manchester, Bromley, Stratton, Okemo, and Magic Mnts. Renovated in 2016, our home has a gourmet kitchen, new bathrooms, washer/dryer, double sided fireplace, woodburning stove, wireless, and great room with HDTV dish network. All beds are new, and/or protected with "sleep tite" pillow & mattress protectors. Pillows are comfortable, blankets are soft and new.

Jun 3 – 10

G$118,624 GYD per night

Guest favorite

Room in Bennington

5.0 out of 5 average rating, 94 reviews

E and E’s B and B Queen Guest Room-Bed & Breakfast

We are located on 16 East Street in Bennington VT minutes from rt 7 and route 9 Main Street. Summer is more like a mini resort with a beautiful in-ground pool and Hot Tub. We also feature plenty of in-room USB phone plug-ins and extensions, in room TVs.. Perfect for couples or bring a child. (Extra Fees for children over 2 years. Sunning Deck or shaded patio dining or just relaxing with a good book poolside or the indoor lounge with a drink. We’ve got you covered. Many unexpected amenities.

Jun 22 – 29

G$25,363 GYD per night

Bed and breakfast in Winhall

4.8 out of 5 average rating, 5 reviews

Bromley View Inn Suite #15

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 fireplace, tons of seating, a bar and worktable. 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.

Oct 22 – 29

G$26,231 GYD per night

Guest favorite

Home in Arlington

5.0 out of 5 average rating, 60 reviews

Charming Farmhouse Retreat+Hot Tub+2.5 Acres+Pets

Experience the rustic charm and modern amenities of Warm Brook Farm, our extensively renovated & historic 1792 Federal-style colonial farmhouse in Arlington, Vermont. Nestled amidst the breathtaking Green Mountains and Taconic Range, this property is the perfect getaway destination for anyone looking to escape the hustle and bustle of city life and embrace the tranquility of rural living. Warm Brook Farm has all the charm of an 18th century home, with all the modern comforts of today.

Sep 24 – Oct 1

G$106,171 GYD per night

Guest favorite

Cottage in Williamstown

4.97 out of 5 average rating, 72 reviews

Artistic Nature Cottage

Kalarama Cottage is a newly renovated space in the middle of nature! Make yourself right at home in this quiet, private and peaceful location. The cottage is overlooking a beautiful forested mountain range, with easy access to hiking, biking, and cross-country ski trails right out the door. Kalarama is bright and sunny with stunning views. Come to unwind, enjoy nature, read, meditate or just work remotely from our 23 acre property!

Jan 17 – 24

G$51,192 GYD per night

Bed and breakfast in Whitingham

The Engel House Room 5: Mt Snow/Wilmington VT Area

Room 5 is one of the original bedrooms of the house and is a comfy place to relax. This large room boasts many windows to get lots of natural light and second floor views of our quaint little village. The attached private bath offers a spa-like experience with a full tub/shower and a light that can give you mood lighting as well as a Bluetooth speaker that can play your own music through your cell phone or wireless device.

Mar 7 – 14

G$37,452 GYD per night

Guest favorite

Room in Bennington

4.92 out of 5 average rating, 13 reviews

Timeless Victorian Coach suite

Spacious room has 10 foot ceilings and hard wood floors. The room is furnished with a four-poster queen size bed, several comfortable chairs, cable television, and a working fireplace (Duraflame logs only, please). The full private bath is equipped with a jetted spa-tub and separate shower. Individually controlled air conditioning and heat plus a ceiling fan for all year comfort

Aug 20 – 27

G$54,936 GYD per night

Guest favorite

Apartment in Pownal

4.94 out of 5 average rating, 180 reviews

The Shepherd's Retreat

This in-law apartment is on the first floor of our 2 level home and has its own separate entrances. It features an open floor plan with galley kitchen and breakfast bar. This location has a peaceful relaxing atmosphere but with easy access to shopping, site seeing, hiking, and is minutes away from historic Bennington, Vt and the Berkshires (Mass Moca Museum).

May 3 – 10

G$22,703 GYD per night

Room in West Dover

4.96 out of 5 average rating, 132 reviews

Bedroom, sitting room, private bath in 1890's home

Private rooms in an 1890's home. Your summer experience in the beautiful green mountains in southern VT starts here. Just minutes from biking, hiking, golf, lakes and shopping. Lighted sidewalks to nearby restaurants and bars. Four amazing museums are in our corner of the world: The Clark Art, Mass MoCA, Bennington Museum, Science Museum.

Mar 25 – 30

G$35,864 GYD per night