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Check prices for these dates

Next weekend
9 Jan - 11 Jan
In two weeks
16 Jan - 18 Jan
In one month
30 Jan - 1 Feb
In two months
27 Feb - 1 Mar

Our top choices for Windsor bed & breakfast

Porch
Harvest Barn Inn

Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (244)
"Gourmet breakfast, quiet and beautiful scenery. Loved it!!!!!"
United States
RICHARD
Harvest Barn Inn
Exterior
Mountain Valley Retreat

Mountain Valley Retreat

Mountain Valley Retreat
2.5 star property
Killington
9.6 out of 10, Exceptional, (191)
"This was my third stay with Mike and Barbara. It's just so lovely in a beautiful rural setting! And sure can't complain about the hearty breakfasts cooked by Chef Mike. It's certain I'll return on another ski adventure to Killington."
United States
Kathy
The price is AED 404
AED 457 total
includes taxes & fees
11 Jan - 12 Jan
Mountain Valley Retreat
Front of property
The Jackson

The Jackson

The Jackson
4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (259)
"The Jackson Inn is incredibly charming and in a picturesque area. The room was very comfortable and the restaurant and staff was amazing."
United States
Abby
The Jackson
Economy Room | Individually decorated, individually furnished, free WiFi, bed sheets
The Vesper

The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (52)
"Charming bed and breakfast"
United States
Nicholas
The price is AED 558
AED 614 total
includes taxes & fees
11 Jan - 12 Jan
The Vesper
Game room
Dexter's Inn

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 AED 964
AED 1,046 total
includes taxes & fees
5 Jan - 6 Jan
Dexter's Inn
Front of property
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (108)
"Great stay at this cozy inn! The innkeeper was very helpful and attentive. The breakfasts were delicious. Comfortable and clean! It would be nice to visit it again in the summer."
United States
Helen
The price is AED 767
AED 836 total
includes taxes & fees
5 Jan - 6 Jan
Stone Hearth Inn and Eatery
Front of property
Snowed Inn

Snowed Inn

Snowed Inn
3.5 star property
Killington
9.8 out of 10, Exceptional, (374)
"A wonderful hotel. The atmosphere is warm and clean."
United States
Fevzi
The price is AED 867
AED 1,049 total
includes taxes & fees
6 Jan - 7 Jan
Snowed Inn
Front of property
Stay At Jimmy's

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 AED 915
AED 1,006 total
includes taxes & fees
5 Jan - 6 Jan
Stay At Jimmy's
Terrace/patio
Deer Brook Inn

Deer Brook Inn

Deer Brook Inn
3.0 star property
Woodstock
The price is AED 1,001
AED 1,102 total
includes taxes & fees
5 Jan - 6 Jan
Deer Brook Inn
Outdoor pool
Echo Lake Inn

Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
8.6 out of 10, Excellent, (98)
"No lake-view. Friendly staff, excellent breakfast."
United States
Wendy
The price is AED 963
AED 1,050 total
includes taxes & fees
4 Feb - 5 Feb
Echo Lake Inn
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.
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Top Windsor Hotel Reviews

Hilton Garden Inn Hanover Lebanon

Hilton Garden Inn Hanover Lebanon

10/10 Excellent
"Front desk clerk was very welcoming and made us aware of all the special service you offer. (Example: the times the breakfast buffet opens, the hours of the bar etc.)"
BETH 1-night trip
Posted 2 days ago
Hilton Garden Inn Hanover Lebanon

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. Situated 12 mi (19.3 km) from the heart of Windsor. Stay At Jimmy's: 3 rooms. Located 11.9 mi (19.1 km) from the core of Windsor. 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.