Book Windsor Bed & Breakfast

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Our top choices for Windsor bed & breakfast

Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (246 reviews)
"Gourmet breakfast, quiet and beautiful scenery. Loved it!!!!!"
United States
RICHARD
$149 nightly
The price is $163
Jan 27 - Jan 28
Total with taxes and fees
Harvest Barn Inn

Mountain Valley Retreat

Mountain Valley Retreat
2.5 star property
Killington
9.6 out of 10, Exceptional, (195 reviews)
"Superb stay all the way around! Mike and Barbara work very hard for their guests and it shows with all the room details and breakfast is 5 out of 5 stars everytime. Check in and out is very easy as well as parking even on snow covered days as the property is very well kept and cleared. Loved it and want to return!"
United States
Steven
$110 nightly
The price is $124
Jan 26 - Jan 27
Total with taxes and fees
Mountain Valley Retreat

The Jackson

The Jackson
4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (262 reviews)
"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
$199 nightly
The price is $219
Jan 25 - Jan 26
Total with taxes and fees
The Jackson

The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (53 reviews)
"Charming bed and breakfast"
United States
Nicholas
$178 nightly
The price is $196
Feb 12 - Feb 13
Total with taxes and fees
The Vesper

Snowed Inn

Snowed Inn
3.5 star property
Killington
9.8 out of 10, Exceptional, (378 reviews)
"We had such a wonderful time at the Snowed Inn and we’re already looking forward to coming back next year! The staff and owners were incredibly warm and friendly, the atmosphere was fantastic, and the location was perfect! Highly recommend!!"
United States
Corey
$235 nightly
The price is $258
Jan 25 - Jan 26
Total with taxes and fees
Snowed Inn

Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (47 reviews)
"Very cool vibe at this very comfortable B&B. Hosts were very friendly and responsive. Would definitely stay here again!"
United States
Thomas
$249 nightly
The price is $274
Jan 26 - Jan 27
Total with taxes and fees
Stay At Jimmy's

Deer Brook Inn

Deer Brook Inn
3.0 star property
Woodstock
$272 nightly
The price is $300
Feb 8 - Feb 9
Total with taxes and fees
Deer Brook Inn

Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (109 reviews)
"So great all around!"
United States
Janet
$288 nightly
The price is $314
Jan 26 - Jan 27
Total with taxes and fees
Stone Hearth Inn and Eatery

Dexter's Inn

Dexter's Inn
3.0 star property
Sunapee
8.8 out of 10, Excellent, (70 reviews)
"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
$263 nightly
The price is $285
Jan 25 - Jan 26
Total with taxes and fees
Dexter's Inn

Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
8.6 out of 10, Excellent, (98 reviews)
"No lake-view. Friendly staff, excellent breakfast."
United States
Wendy
$283 nightly
The price is $309
Jan 27 - Jan 28
Total with taxes and fees
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

Find out more about Windsor

Windsor B&B information

Number of reviews
1,418
Accommodation
26 B&B
Lowest Price
$124
Highest Price
$314

Frequently asked questions

What is the nightly rate for a Bed and Breakfast in Windsor?
Prices for B&Bs in Windsor often vary, but you can find a great deal from $124 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Windsor B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a Bed & Breakfast in Windsor?
The best time to book a B&B in Windsor is during the late spring and summer months, particularly from May through September. This peak season invites travelers to immerse themselves in the vibrant local culture, with numerous outdoor festivals and events that showcase the area's charm and hospitality. The pleasant weather, with temperatures typically ranging from the mid-60s to low 80s Fahrenheit, makes it an ideal backdrop for leisurely strolls along the waterfront, wine tasting tours, and exploring the nearby parks.

June is particularly popular, as it heralds the start of summer festivities, including music events and farmers' markets brimming with fresh local produce. The lively atmosphere of the town, combined with the colorful gardens in full bloom, offers a delightful experience for those seeking to connect with the community.

For those looking for a more budget-friendly option, consider visiting in late fall, around November. This time offers a quieter ambiance, great for enjoying the beautiful autumn foliage and indulging in local culinary delights without the hustle and bustle of peak tourist season.
What is the difference between a Windsor B&B and a hotel?
Every Windsor B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Windsor B&Bs.

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