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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Top guest favorite

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 two-story cabin is surrounded by a blanket of fresh snow, with trees in the background and a clear blue sky above. The building features large windows, showcasing a sloped roof and a stone chimney. The pathway is partially cleared, leading to the entrance.

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

The historic Windsor Mansion is situated atop a gentle hill, surrounded by lush greenery and trees in various shades of green. The white exterior of the mansion stands out against the natural backdrop, with many windows reflecting the sky above.

Private room in Windsor

4.88 out of 5 average rating, 82 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

Guest favorite

A historic brick building is framed by verdant trees and a white picket fence. The entrance features large windows and shutters, with a flag displayed prominently. A sign indicating the property name is visible by the pathway, contributing to the charming exterior.

Hotel room in Tunbridge

5 out of 5 average rating, 38 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.

Guest favorite

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.

Top guest favorite

Private room in Bridgewater

4.99 out of 5 average rating, 173 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.

Superhost

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

The exterior of a vibrant red building is displayed, featuring multiple stories and architectural details such as white trim. Snow covers the surrounding ground, and a light dusting is present on the roof. A paved driveway leads to a parked vehicle, and a whimsical yellow structure adds a pop of color.

Private room in Weathersfield

5 out of 5 average rating, 34 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!

Top guest favorite

Private room in Hartland

4.98 out of 5 average rating, 266 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.

Top guest favorite

A welcoming entryway features a spiral staircase leading to the upper levels. A vintage chandelier hangs from the ceiling, providing warm light. A decorative rug lies on the hardwood floor, and a classic red sofa is positioned against the wall, accompanied by an antique side table.

Private room in Norwich

4.97 out of 5 average rating, 147 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

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

A large, bare tree stands prominently in the foreground, surrounded by a carpet of fallen orange and yellow leaves. In the background, a lush green landscape is visible, dotted with trees and a serene pond reflecting the clear blue sky.

Farm stay 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 Inn/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, ducks & chickens.