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Bed and breakfast vacation rentals in Windsor County

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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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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.

Private room in Hartland

4.98 out of 5 average rating, 473 reviews

Spacious King Suite - Fireplace and Mountain Views

The Atwater Room – your retreat in the Upper Valley. This spacious suite features a cozy fireplace, mountain views, and a private bathroom with a clawfoot tub and shower. Enjoy the luxurious king-sized bed and serene ambiance. Located just 15 minutes from Quechee, Norwich, Hanover, and Lebanon, and close to Woodstock (25 minutes) and Killington (39 minutes). Your stay includes a self-serve breakfast with granola, yogurt, fruit, coffee, and tea. You'll also have access to the guest kitchen.

Private room in Windsor

4.89 out of 5 average rating, 70 reviews

Stay at the largest Colonial Revival Mansion in US

Built in 1902 and comprehensively renovated in late 2016, the Windsor Mansion is an incredibly well preserved example of Colonial Revival Architecture. Filled with elegance & history, Three US Presidents have slept here. Our 17 Rooms/Suites are individually decorated each with private bathroom & free wireless internet. Set on 14 acres with a tiered terrace offering spectacular views & a custom fire pit. Lots to see in area including Saint-Gaudens Nat'l Park, Woodstock, Dartmouth College,etc

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.

Private room in Barnard

4.91 out of 5 average rating, 87 reviews

The Fan House 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 (lower gondola), 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.

Private room in Bridgewater

4.99 out of 5 average rating, 159 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.

Private room in Woodstock

4.85 out of 5 average rating, 13 reviews

Bedroom in The Bunkhouse

Wise Pines is a Holistic & Sustainable B&B/Hostel that offers a unique farm experience. In the rural woods of Vermont, this private room can accommodate 2 people and may be shared with up to 10 other people in this two level renovated barn. There is a small seating area and a large upper deck that over looks the property. The barn 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.

Private room in West Windsor

4.85 out of 5 average rating, 86 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

Private room in Weathersfield

5 out of 5 average rating, 19 reviews

The Oak 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!

Private room in Norwich

4.96 out of 5 average rating, 137 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!

Private room in Woodstock

4.88 out of 5 average rating, 8 reviews

YOKO: Modern design in the heart of the Village

The Vesper Bed and Breakfast, located just off the village green in Woodstock Vermont, is an 1835 Greek Revival home with a modern, sustainable vision for bringing community together. It's thoughtful, vibrant interior and nourishing food bring a positive energy to all the adventurous folks it attracts. Run by a small family who imbue the space with humor and heart, it's a basecamp for getting outside, going inward and enjoying it all.

Private room in Killington

4.93 out of 5 average rating, 123 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.

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Cabins

Kick off your hiking boots at these rustic lodgings

Chalets

Adventure-ready homes with après-ski style

Popular amenities for Windsor County bed and breakfast rentals

Free parking on premises

Air conditioning

Family-friendly bed and breakfast rentals

Private room in Norwich

4.83 out of 5 average rating, 104 reviews

The Partridge House Room 202

Private room in Killington

5 out of 5 average rating, 15 reviews

Efficiency Apartment with Queen and Twin over Queen Bunk - The Trailside Inn

Private room in Proctorsville

5 out of 5 average rating, 14 reviews

Old Stage Room - Golden Stage Inn

Private room in Shrewsbury

4.96 out of 5 average rating, 53 reviews

Balm of Gilead B & B Blue Suite

Private room in Norwich

4.92 out of 5 average rating, 84 reviews

The Partridge House Room 203

Private room in Mount Holly

4.98 out of 5 average rating, 54 reviews

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

Private room in Shrewsbury

4.91 out of 5 average rating, 34 reviews

Balm of Gilead B & B Pink Suite

Private room in Killington

4.8 out of 5 average rating, 15 reviews

Twin Room with Private Bath - The Trailside Inn

Bed and breakfast rentals with breakfast

Private room in Killington

5 out of 5 average rating, 9 reviews

Queen & Twin Room with Private Bath- Trailside Inn

Private room in Barnard

4.88 out of 5 average rating, 65 reviews

The Fan House, A Vermont Country Home

Private room in Ludlow

5 out of 5 average rating, 3 reviews

The Governor's Inn - Sally's Room

Private room in Killington

4.86 out of 5 average rating, 7 reviews

(2) Twin Bunk Bed Private Room - The Trailside Inn

Private room in Ludlow

5 out of 5 average rating, 10 reviews

The Governor's Inn - Ann's Room

Private room in Killington

4.75 out of 5 average rating, 4 reviews

Queen with Twin Bunk Bed - The Trailside Inn

Private room in Ludlow

5 out of 5 average rating, 4 reviews

The Governor's Inn - Abigail's Room

Private room in Royalton

4.74 out of 5 average rating, 99 reviews

Glamping Barn Space

Bed and breakfast rentals with a patio

Private room in Chester

5 out of 5 average rating, 38 reviews

Farm at Williams River House - Essex Suite

Private room in Chester

5 out of 5 average rating, 20 reviews

Farm at Williams River House - Gloucester Suite

Private room in Chester

5 out of 5 average rating, 18 reviews

Farm at Williams River House - Hawthorne Suite-ADA

Destinations to explore