Bed and breakfast vacation rentals in Windham County

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Top-rated bed and breakfast rentals in Windham County

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Guest favorite

An outdoor fire pit is surrounded by several Adirondack chairs set on a stone patio. In the background, a wooden structure is visible, alongside a hot tub, with a gently sloped lawn dotted with rocks and trees framing the peaceful scene.

Home in Wilmington

4.98 out of 5 average rating, 45 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!

Cabin in Peru

5 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.

A spacious lounge area features a central fireplace surrounded by a large, U-shaped wooden seating arrangement with colorful cushions. A bar is visible in the background, along with large windows allowing natural light to fill the room. Wooden beams and stars add character to the ceiling.

Private room in Winhall

4.86 out of 5 average rating, 7 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.

Guest favorite

A spacious sleeping area features two large beds with soft linens, positioned under skylights that fill the room with natural light. Wood beams and a warm wood floor enhance the rustic charm, while large windows overlook the surrounding trees.

Apartment in Dummerston

4.92 out of 5 average rating, 403 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. If you'd like to book a healing retreat I offer Reiki sessions to guests. Inquire when you book. *Mount Snow is 35 minutes away. Okemo, Stratton, Bromley and Magic is 1 hour away and Stratton is 1 hour away.

Guest favorite

Private room in Halifax

4.97 out of 5 average rating, 31 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

Guest favorite

A spacious bedroom features a four-poster bed dressed in white linens and plush pillows. Two bedside tables with lamps flank the bed. A round mirror hangs above a chair beside a small table, while a plush area rug lies underfoot. Windows are adorned with drapes.

Private room in Chester

5 out of 5 average rating, 39 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.

Superhost

A spacious bedroom features a King bed with neutral bedding positioned against a wooden accent wall. Soft lighting is provided by bedside lamps. A bench sits at the foot of the bed, while a single chair and a small table are nearby. Natural light enters through a window.

Private room in Dover

5 out of 5 average rating, 8 reviews

Classic King with balcony in Historic Inn, rm 8

Luxury King room with balcony in renovated Historic Inn. This room is upstairs and has a King bed and full bath with bathtub and shower. Room comes with towels, toilet paper, shampoo, conditioner, body lotion and other toiletries. The balcony has a bistro set for enjoying a coffee or happy hour. This unit also has a mini fridge and coffee maker. We provide Keurig K-cups, coffee creamer, tea, sugars and various snacks. Inn room 8 is not pet friendly.

Home in West Brattleboro

4.85 out of 5 average rating, 20 reviews

Unique 2BR - Great Monthly Rate! - Pet Friendly!

Welcome to the Culbertson House The Culbertson House is an exceptional gem in Brattleboro, Vermont. You're not going to find a more interesting, comfortable and beautiful place to stay. Built in 1923, this historic home is spacious, unique, a little bit quirky, surrounded by Vermont forest yet close to town. Two bedrooms, two bathrooms, full stocked kitchen, large living room with 50" TV. A complete home ready to move into!

Guest favorite

A cozy bedroom features a queen bed with soft linens and a large area rug. Natural light enters through two windows beside a comfortable armchair. A sliding glass door provides access to a balcony overlooking the lush greenery, creating a serene ambiance.

Private room in Guilford

5 out of 5 average rating, 8 reviews

Welcoming B&B room with balcony and whirlpool bath

Spacious and comfortable room with queen bed, private bath, whirlpool with heated towels and balcony overlooking the birdfeeders in the backyard gardens and the Green River. All located in an updated 1830 Bed & Breakfast surrounded by foliage. Beautiful shaded dirt roads run by the inn, as well as the Guilford covered bridge just 50 feet from the front door. Sumptuous breakfast is included with your room. Come and relax!

Guest favorite

Private room in Town of Rockingham

5 out of 5 average rating, 123 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.

Guest favorite

Private room in Town of Rockingham

4.99 out of 5 average rating, 86 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 :)

A double twin room features two wooden beds with intricate posts, positioned parallel to each other. Soft white bedding covers the beds, while a patterned area rug enhances the space. Complementary wall sconces provide illumination, and a door leads to the adjoining bathroom.

Private room in Newfane

4.82 out of 5 average rating, 11 reviews

Yogi & artist retreat center

This double twin room is one of 6 rooms in a gorgeous retreat center complete with a yoga studio, library and living area. The room has an en-suite bath. Continental breakfast included. Outdoor grilling, fire pit, 100 acres of walking trails. Willow is a one-of-a-kind retreat center nestled in the gorgeous village of South Newfane.