Bed and breakfast vacation rentals in Windsor County

Find and book unique bed and breakfast rentals on Airbnb

Top-rated bed and breakfast rentals in Windsor County

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

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Top guest favorite

A charming home with a dark wood exterior is surrounded by well-tended gardens. Vibrant flowers in shades of pink and red flourish in the foreground, while abundant greenery enhances the inviting landscape. Large windows and a shaded porch reflect a cozy atmosphere, blended with the natural surroundings.

Private room in Mount Holly

4.98 out of 5 average rating, 62 reviews

Fenn Farmstead - w/farm-to-table breakfast 1 BR

Paradise in Vermont’s Green Mountains! On a quiet, scenic, country road, our spacious home has all the comforts for a good night’s rest with a delicious farm to table breakfast. Ski Okemo or Killington. In summer find over 75 recorded species of birds, enjoy the gardens and learn about sustainable agriculture. Pick raspberries and blueberries in July and August. In autumn enjoy Vermont's spectacular leaf colors. **Now hosting only guests with complete, verifiable Covid-19 vaccine plus booster.**

A charming house is nestled among tall snow-covered trees, with a sloped roof reflecting the bright winter sky. The surrounding landscape features a blanket of fresh snow, creating a serene and quiet winter atmosphere.

Private room in Shrewsbury

4.91 out of 5 average rating, 34 reviews

Balm of Gilead B & B Pink Suite

Great views. Spacious indoor and out. Wonderful for couples, solo adventurers, business travelers, families (with kids), groups of friends, and furry friends (pets). I can accommodate small weddings, meetings and and parties with a variable facility fee. I am a Bed and Breakfast, and have 2 suites available. The other one is listed under Balm of Gilead B & B Blue suite. More pictures there. Airbnb doesn't provide me with an option for both suites on one site, but you can book each individually.

The exterior of the cabin is illuminated by moonlight, showcasing a mix of log and modern architecture. Snow-covered grounds highlight the inviting entrance, while warm lights glow from the windows, suggesting a cozy atmosphere inside the home. A clear night sky is visible above.

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.

Guest favorite

Double French doors adorned with a simple green wreath are flanked by snow-covered greenery. The entrance is partially hidden by a blanket of fresh snow, creating a serene winter scene.

Private room in Barnard

4.88 out of 5 average rating, 66 reviews

The Fan House, A Vermont Country Home

Guest rooms and kitchen licensed by state of Vermont with 100% cleanliness score from the VT Dept of Health. The Fan House is a historic 1840 property, 10 minutes from Woodstock village, 25 minutes to Killington Ski Resort (gondola on Rt. 4), 15 miles to Vermont Law School, five miles to the Appalachian Trail and one mile to the Barnard Inn Restaurant and yoga studio. Stunning grounds feature an English Garden that blooms from spring to autumn. Silver Lake State Park is around the corner.

Guest favorite

A wooden railing overlooks a gently flowing stream framed by lush greenery. Sunlight filters through the trees, highlighting the vibrant foliage and creating a serene outdoor setting. In the background, rolling hills are visible, enhancing the natural charm of the landscape.

Hotel room in Tunbridge

5 out of 5 average rating, 37 reviews

Historic Hubble Shire Farm Inn--French Queen

An historic federal meets modern design with this impeccably resurrected home from 1832 situated just steps from the village greens of Chelsea, a quintessential Vermont town. All modern electrical, plumbing, bathrooms with all the historical charm of the 1830s. The French Queen features a queen hand carved bed, 19th century French commode and nightstands, elegant porcelains, a lounge chair and decorative fireplace and large private bath across the hall. A gourmet breakfast is included.

Top guest favorite

Private room in Bridgewater

4.99 out of 5 average rating, 172 reviews

MT Retreat / Killington, Woodstock, Rutland, Okemo

We also offer our beautiful grounds as a venue for tented events. Bewitching views. Quiet, private suite. C. bkfst. Winter garage! COVID: “VT Forward” guidelines followed. Consider a private cooking class from award-winning Chef Ted and enjoy the foods of your labor in a lovely natural setting. BYOB. See Odyssey Events VT & Airbnb Experiences for cooking options. FYI, Bedroom size: 9' x 14'. Adjoining bathroom: 8' x 9'. The ante-room/office: 8' x 12', which is also yours to use.

Guest favorite

A quaint Vermont cape house is set amidst lush greenery. The building features a steeply pitched roof with a chimney, surrounded by well-maintained gardens and tall trees. A gravel drive leads up to the entrance, completing the serene rural setting.

Private room in West Windsor

4.85 out of 5 average rating, 87 reviews

Thorny Hills Farm

Private upstairs suite that sleeps up to 6 people. 1 bedroom with a queen sized bed & a bedroom suite with 4 single beds. Sitting area with tables allow for relaxing or group meals. Private bath serves the suite. Mini frig, microwave & coffee maker with grill outside. Private entrance & patio. Perfect for local horse events. No smokers. Not suitable for young children under 10. Check in is 4PM but can be adjusted if needed. Check out is 10AM. Additional guests $35/night

Top guest favorite

A warm entryway features dark double doors framed by intricate glass panels. A wooden bench is positioned on one side, with a rustic lamp nearby. The walls are lined with natural wood, and a mounted deer head adds a touch of nature to the interior.

Private room in Weathersfield

5 out of 5 average rating, 21 reviews

The Pine Room - Ladoga

Grand opening! Your own oasis on the outskirts of a VT town. Surrounded by nature trails & forests with plenty of outdoor activities. Short drive away from Mt. Ascutney, Okemo, historic landmarks, and shopping across the NH border. Room is on the second floor and features a private bathroom with shower, a mini-fridge, smart TV (w/ Netflix), wi-fi, and a king-size bed. All bedding / toiletries are provided. Just bring your toothbrush! 8 gbit fiber optic is coming in March '24!

Top guest favorite

The exterior of a charming white house is surrounded by lush green trees. A spacious porch with multiple seating options offers a view of the gentle landscape. The roof is adorned with dormer windows, enhancing its traditional design.

Private room in Hartland

4.98 out of 5 average rating, 260 reviews

Spooner House - Gates Room with Private Bath

The Spooner House - Enjoy the peaceful countryside of Hartland, just minutes from Quechee, Woodstock, Norwich, Lebanon, Hanover, and White River Junction. The Gates Room features a queen-sized bed, private bathroom, and a desk with mountain views, perfect for remote work with our 100GB fiber internet. Your stay includes a self-serve breakfast with homemade granola, yogurt, fresh fruit, espresso drinks, and tea. You'll also have access to the shared kitchen and parlor.

Guest favorite

A historic brick home is presented, featuring a centrally located entrance flanked by large windows. The white picket fence and stone pathway lead to the inviting front door. The house is set within a landscaped yard, showcasing a blend of greenery and elegant architectural details.

Private room in Norwich

4.97 out of 5 average rating, 144 reviews

The Partridge House Room 201

A beautifully remodeled historic home seconds from downtown Norwich Vermont, and a five minute drive from Dartmouth College and Hanover, New Hampshire. We are good for couples, solo adventurers, business travelers, families (with kids), and big groups. We have a proper dining room and 2 beautiful sitting rooms. We offer complimentary coffee, tea, cappuccino, and latte as well as flexible breakfast options. We love having guests and hope to see you soon!

Guest favorite

The exterior of the farmhouse showcases a spacious, two-story building with a dark roof, nestled among lush green lawns and surrounded by colorful fall foliage. Rolling hills and mountains provide a scenic backdrop, highlighting the natural beauty of the Vermont landscape.

Private room in Killington

4.93 out of 5 average rating, 128 reviews

King Room with Private Bath - The Trailside Inn

This classic farmhouse has everything you could hope for in your Vermont vacation. You'll love the Trailside Inn! This listing is for a King Room in the main inn. All of our rooms have full private bathrooms. The maximum occupancy for this room is 2 guests. We are offering continental breakfast, coffee and tea service daily. For more than 2 travelers, ask about our larger room options.

Superhost

The treehouse is nestled among autumn foliage, featuring wooden steps leading to a raised deck. Sunlight filters through the trees, casting shadows on the ground covered in fallen leaves. A colorful hammock hangs nearby, providing a spot for relaxation.

Private room in Woodstock

5 out of 5 average rating, 4 reviews

3 Building Farm Stay at Wise Pines (16 guests)

Wise Pines is a Holistic & Sustainable B&B/Hiker Hostel that offers a unique farm experience. The property has 2 treehouses (for lodging) and a 12 person renovated barn with 2 private rooms and a bunkroom. Wise Pines sits on 40 acres of land, complete with walking/hiking trails and a pond to sit by and enjoy. The owners live on property with their dogs, goats & chickens.