A snow-covered river valley with a bridge and a town.

Book Windsor Bed & Breakfast

Check prices for these dates

Next weekend
Jul 24 - Jul 26
In two weeks
Jul 31 - Aug 2
In one month
Aug 14 - Aug 16
In two months
Sep 11 - Sep 13

Our top choices for Windsor bed & breakfast

Interior

The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (67 reviews)
"Great place to live and the owner is very friendly!"
United States
Qing
$150 nightly
The price is $165
Jul 26 - Jul 27
Total with taxes and fees
The Vesper
Restaurant

The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (295 reviews)
"Everything was terrific! Great vibe & location."
United States
Brian
$179 nightly
The price is $197
Jul 21 - Jul 22
Total with taxes and fees
The Jackson
Front of property

Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (49 reviews)
"Wonderful amenities, location, and team, Highly recommend and would love to stay again"
United States
Heather
$249 nightly
The price is $274
Jul 26 - Jul 27
Total with taxes and fees
Stay At Jimmy's
Front of property

Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (120 reviews)
"Friendly helpful clean. Bathroom clean. Nice pillows. A/c was super because it was very hot outside. Breakfast was very good"
United States
Kathleen
$230 nightly
The price is $251
Jul 20 - Jul 21
Total with taxes and fees
Stone Hearth Inn and Eatery
Interior

Deer Brook Inn

Deer Brook Inn
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (3 reviews)
"The property manager greeted us when we walked in and she was extremely friendly and kind. The inn was charming and had a homey feel, and the rooms were very clean and well maintained with awesome amenities."
United States
Sara
$233 nightly
The price is $256
Aug 2 - Aug 3
Total with taxes and fees
Deer Brook Inn
Porch

Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (268 reviews)
"Amazing property and hosts...If you are looking for a quiet getaway with a river view and gourmet breakfast, look no further!"
United States
Paul
$168 nightly
The price is $183
Aug 10 - Aug 11
Total with taxes and fees
Harvest Barn Inn
Exterior

Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
8.6 out of 10, Excellent, (100 reviews)
"Food was excellent. Room was clean and cozy. Staff were all incredibly welcoming and friendly. Perfect location. Would highly recommend. "
United States
Danielle
$203 nightly
The price is $221
Jul 22 - Jul 23
Total with taxes and fees
Echo Lake Inn
Game room

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
$256 nightly
The price is $278
Jul 19 - Jul 20
Total with taxes and fees
Dexter's Inn
Front of property

Snowed Inn

Snowed Inn
3.5 star property
Killington
9.8 out of 10, Exceptional, (399 reviews)
"Very convenient location with warmth and wonderful hosts."
United States
Martin
$141 nightly
The price is $155
Jul 21 - Jul 22
Total with taxes and fees
Snowed 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

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

8/10 Good
"We stayed for 5 nights. When we asked about additional towels we were told that there would be an 11.00 charge for them to come and service the room. The other option that they presented was for us to wash our towels ourselves. They do provide the machines and soap, though. The staff was friendly but some of the hotel showed signs of deferred maintenance."
Todd 5-night trip
Posted less than an hour ago
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Find out more about Windsor

Windsor B&B information

Number of reviews
1,271
Accommodation
38 B&B
Lowest Price
$155
Highest Price
$278

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 $155 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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