Find Windsor Bed And Breakfast

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Dec 5 - Dec 7
In two weeks
Dec 12 - Dec 14
In one month
Dec 26 - Dec 28
In two months
Jan 23 - Jan 25

B&B in Windsor

Exterior
Mountain Valley Retreat

Mountain Valley Retreat

2.5 star property
Killington
9.6 out of 10, Exceptional, (189)
"Absolutely lovely stay!"
United States
Elizabeth
The price is ￥17,178
￥19,411 total
includes taxes & fees
Nov 30 - Dec 1
Mountain Valley Retreat
Front of property
The Jackson

The Jackson

4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (251)
"Very cute inn, the restaurant was a plus. Had a great dinner there and def will come back. "
United States
Jaunita
The Jackson
Front of property
Snowed Inn

Snowed Inn

3.5 star property
Killington
9.8 out of 10, Exceptional, (370)
"The inn truly stands out for it's naturally beautifully decorated all bright wooden interior. Their recent breakfast area expansion is wonderfully bright and cheery, as are the hosts. Thank you and we are looking forward to seeing you again!"
United States
Bradford
The price is ￥27,640
￥33,444 total
includes taxes & fees
Dec 3 - Dec 4
Snowed Inn
Front of property
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3.0 star property
Chester
9.2 out of 10, Wonderful, (106)
"Good breakfast and dinner options. Great location for hiking."
United States
Paul
The price is ￥29,032
￥31,645 total
includes taxes & fees
Dec 8 - Dec 9
Stone Hearth Inn and Eatery
Terrace/patio
Room in Historic Inn! 20 Minutes to Okemo!

Room in Historic Inn! 20 Minutes to Okemo!

Chester Depot
9.2 out of 10, Wonderful, (18)
"The Chester Inn was beautiful and located in downtown Chester. "
United States
Peter C.
The price is ￥15,530
￥26,178 total
includes taxes & fees
Nov 30 - Dec 1
Room in Historic Inn! 20 Minutes to Okemo!
Economy Room | Individually decorated, individually furnished, free WiFi, bed sheets
The Vesper

The Vesper

3.0 star property
Woodstock
9.2 out of 10, Wonderful, (46)
"Cute B&B, great location! Easy walk to coffee house and downtown area. We really enjoyed our stay!"
United States
Roger
The price is ￥24,010
￥26,411 total
includes taxes & fees
Dec 1 - Dec 2
The Vesper
Dining
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!

Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!

Chester Depot
9.0 out of 10, Wonderful, (2)
"Property seemed well-maintained and cared for. We were only there a short time, but it was well put together. The check-in process was a little hectic, check in time was 3pm, but our room wasn't ready. The caretaker was very friendly. We only had to wait about 20 minutes. We weren't aware this property was a VRBO, and not a regular Inn. "
United States
Jacque
The price is ￥13,961
￥25,300 total
includes taxes & fees
Nov 30 - Dec 1
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
Front of property
Stay At Jimmy's

Stay At Jimmy's

3.0 star property
Woodstock
10.0 out of 10, Exceptional, (46)
"Very cool vibe at this very comfortable B&B. Hosts were very friendly and responsive. Would definitely stay here again!"
United States
Thomas
The price is ￥31,076
￥34,184 total
includes taxes & fees
Dec 3 - Dec 4
Stay At Jimmy's
Game room
Dexter's Inn

Dexter's Inn

3.0 star property
Sunapee
8.8 out of 10, Excellent, (70)
"This was my 3rd time staying at Dexter’s Inn and hopefully not the last. It is a wonderful inn with easy access to Mount Sunapee. "
United States
Lisa
The price is ￥38,650
￥41,935 total
includes taxes & fees
Dec 2 - Dec 3
Dexter's Inn
Outdoor pool
Echo Lake Inn

Echo Lake Inn

2.5 star property
Plymouth
8.6 out of 10, Excellent, (98)
"Old fashioned inn with wonderful hosts."
United States
James
The price is ￥42,063
￥45,848 total
includes taxes & fees
Dec 2 - Dec 3
Echo Lake Inn
Front of property - evening/night
Woodbridge Inn

Woodbridge Inn

3.0 star property
Woodstock
9.6 out of 10, Exceptional, (67)
"Staff was very friendly and welcoming "
United States
Michael
The price is ￥69,807
￥76,788 total
includes taxes & fees
Dec 11 - Dec 12
Woodbridge Inn
1 bedroom, desk, iron/ironing board, free WiFi
Honeymoon Suite with Jacuzzi Tub in Historic Inn

Honeymoon Suite with Jacuzzi Tub in Historic Inn

Chester Depot
8.6 out of 10, Excellent, (7)
"Charming place, hope to go back soon."
United States
Sharon S.
The price is ￥21,962
￥34,085 total
includes taxes & fees
Nov 30 - Dec 1
Honeymoon Suite with Jacuzzi Tub in Historic Inn
Interior
King & Queen Suite in Historic Inn Circa 1780

King & Queen Suite in Historic Inn Circa 1780

Chester Depot
9.8 out of 10, Exceptional, (16)
"Central for our needs. easy check in process. Lovely large room with comfy beds. "
United States
HIlary H.
The price is ￥43,569
￥63,139 total
includes taxes & fees
Dec 1 - Dec 2
King & Queen Suite in Historic Inn Circa 1780
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windsor Hotel Reviews

The Shire Woodstock

The Shire Woodstock

10/10 Excellent
"Clean good service and location "
Thomas 1-night trip
Posted 3 days ago
The Shire Woodstock

Find out more about Windsor

Windsor B&B information

Number of reviews
1,240
Accommodation
26 B&B
Lowest Price
￥19,411
Highest Price
￥76,788

Frequently asked questions

Searching for B&Bs in Windsor?
If you're looking for something a little quirkier than your standard hotel experience, a stay at a bed and breakfast could be the perfect alternative for your getaway. While you're here, you can get to know Windsor by exploring its natural beauty. Consider a stop by Paradise Park and Path of Life Garden.
Are you thinking about a B&B for your stay?
With attentive service, opportunities to interact with the owner, and hearty breakfasts, B&Bs offer a unique setting.
What are the best bed and breakfasts in Windsor?
Here are some well-liked B&Bs in the area: The Jackson: 11 rooms. 12.2 mi (19.7 km) from the heart of Windsor. Enjoy the designer toiletries and library. The Vesper: 9 rooms. 12 mi (19.3 km) from the downtown core. Stay At Jimmy's: 3 rooms. 11.9 mi (19.1 km) from the heart of downtown. Enjoy the jetted tubs and private yard.
What's the best time of year to book my B&B in Windsor?
When you're planning your stay in Windsor, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 62°F, while the coldest months are January and February with an average of 22°F. The snowiest months in Windsor are March, January, November, and February, with each month seeing an average of 15 inches of snowfall.
What is there to do in Windsor?
When you want to spend some time in the great outdoors, Connecticut River and Paradise Park are some notable spots. You might put American Precision Museum and Harpoon Brewery on your list if you want to see more of the area.
How can I get to and around Windsor?
You can plan your excursions in and around Windsor ahead of time with these transportation options. Fly into Lebanon, NH (LEB-Lebanon Municipal), which is located 10.7 mi (17.3 km) from the city center. Otherwise, you can search for flights to Springfield, VT (VSF-Hartness State), which is 11.7 mi (18.8 km) away. If you'd like to explore around the area, consider renting a car to take in more sights.

Explore a world of travel with Expedia