Bed and breakfast vacation rentals in Windham County

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Top-rated bed and breakfast rentals in Windham County

Guests agree: these bed and breakfast rentals are highly rated for location, cleanliness, and more.

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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!

Oct 2 – 9

G$218,580 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$170,988 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$118,797 GYD per night

Guest favorite

Room in Guilford

5.0 out of 5 average rating, 13 reviews

Beautiful B&B room by a river and covered bridge.

No detail is overlooked at this charming and upscale place to stay. Crisp, clean rooms with ensuite bathrooms in a beautifully remodeled 1830s home. Gourmet breakfasts are included with your room. Served in our elegant dining room or alfresco on the porch overlooking the gardens and the river. We are within 100 feet of the covered bridge and swimming at the dam. Relax watching the birds at the feeder, sit on the rocks in the river beside our gardens or bike the beautiful country roads.

Oct 29 – Nov 5

G$30,583 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$26,269 GYD per night

Room in Halifax

4.97 out of 5 average rating, 29 reviews

Baked Apples at Shearer Hill Farm B&B Room 1

Baked Apples at Shearer Hill Farm BB, [just 5 miles from center of Wilmington] opened in 1990 and is a small working farm. We are located on a pristine country road. We have large rooms with private baths and a large common sitting room and dining room. Our rooms can either be king beds or twin beds and some rooms can add an extra child or two [additional charge] Our breakfast starts with baked apples and ice cream every morning. Your innkeepers are Bill and Patti Pusey

May 6 – 13

G$35,854 GYD per night

Superhost

Guesthouse in Newfane

5.0 out of 5 average rating, 3 reviews

Queen bed + private bath, breakfast included

This cozy queen room has 2 exposures and a private en-suite bath. Three night stays are tax free—an automatic 9% discount will be applied to your booking. Week-long stays save 27%. Amenities: free breakfast (see description); access to yoga studio, large living room, library and dining room; outdoor grilling, fire pit, 100 acres of walking trails. The Vermont Village Retreat is a one-of-a-kind estate nestled in the gorgeous village of South Newfane.

Oct 3 – 10

G$37,126 GYD per night

Guest favorite

Room in Chester

5.0 out of 5 average rating, 37 reviews

Farm at Williams River House - Essex Suite

Beauty, luxurious comfort, and cozy charm combine in this 1780s farm house nestled between mountains and the fertile Williams River valley. Snuggle into your queen bed, enjoy an espresso in the library, skate on our private rink, or XC ski, snowshoe and stroll along the fields, forests, and river. A delicious farm breakfast featuring local seasonal foods is served daily. We strive to reduce our carbon footprint with solar. ~25min drive to Okemo.

Jun 5 – 12

G$47,522 GYD per night

Guest favorite

Apartment in Dummerston

4.93 out of 5 average rating, 366 reviews

~Serene Barn Retreat~

Peaceful, romantic retreat in this stunningly large, 1850's remodeled barn apartment. The historic barn is nestled into hundrends of acres of Nature Conservency. Many old maple and pine trees, hiking trails and breathtaking views will welcome you along the the drive here. *Mount Snow is 35 minutes away. Okemo, Stratton, Bromley and Magic is 1 hour away and Stratton is 1 hour away.

Jul 11 – 18

G$24,759 GYD per night

Guest favorite

Room in Town of Rockingham

5.0 out of 5 average rating, 108 reviews

Eva Blake House-Margaret's Room

Do you like staying in historic homes? Welcome to the Eva Blake House. Great served breakfasts available between 8 and 10 AM. Three common areas. Abundant amenities. A walk or short drive to The Square with its shops, art galleries, restaurants and movie theater. Margaret's Room has one double bed. A walk down the hall: your large, private bathroom with shower.

May 25 – Jun 1

G$26,231 GYD per night

Guest favorite

Room in Town of Rockingham

4.99 out of 5 average rating, 74 reviews

Visit your Craftsman home away from home-Rm 2 of 2

Turn of the century Craftsman home with charm and great character! We have two bedrooms to offer and bedroom 2 has a full/double mattress perfect for one or two people. Full bathroom is dedicated to guests. Ample parking on and off street. See King bedroom posting (Craftsman Home Away from Home 1 of 2) if you'd like to rent both rooms or just want more space :)

Oct 21 – 28

G$15,858 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$35,916 GYD per night