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, (257 reviews)
"Staff were wonderful, food was excellent, environment was peaceful, everything was clean and in decent condition."
United States
Charles
$144 nightly
The price is $157
Apr 20 - Apr 21
Total with taxes and fees
Harvest Barn Inn

Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (118 reviews)
"Great stay! Very cozy and homey. Very yummy breakfast! "
United States
Olena
$197 nightly
The price is $215
Apr 20 - Apr 21
Total with taxes and fees
Stone Hearth Inn and Eatery

The Vesper

The Vesper
3.0 star property
Woodstock
9.4 out of 10, Exceptional, (58 reviews)
"Uniqueness of rooms, breakfast options and walking distance to so many great spots!"
United States
Emily
$156 nightly
The price is $172
Apr 19 - Apr 20
Total with taxes and fees
The Vesper

The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (278 reviews)
"Easy Check-In; Lovely Room; Great Location & Atmosphere. The staff was very friendly,"
United States
Michael
$169 nightly
The price is $186
May 19 - May 20
Total with taxes and fees
The Jackson

Deer Brook Inn

Deer Brook Inn
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (1 review)
"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
$248 nightly
The price is $273
May 14 - May 15
Total with taxes and fees
Deer Brook Inn

Sleep Woodstock Mobility Impaired Accessible Suite

Sleep Woodstock Mobility Impaired Accessible Suite
Woodstock
$114 nightly
The price is $125
Apr 19 - Apr 20
Total with taxes and fees
Sleep Woodstock Mobility Impaired Accessible Suite

Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
$114 nightly
The price is $125
Apr 19 - Apr 20
Total with taxes and fees
Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
$114 nightly
The price is $125
Apr 19 - Apr 20
Total with taxes and fees
Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
$119 nightly
The price is $131
Apr 19 - Apr 20
Total with taxes and fees
Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
$119 nightly
The price is $131
Apr 19 - Apr 20
Total with taxes and fees
Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
$119 nightly
The price is $131
Apr 19 - Apr 20
Total with taxes and fees
Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
$119 nightly
The price is $131
Apr 19 - Apr 20
Total with taxes and fees
Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
$114 nightly
The price is $125
Apr 20 - Apr 21
Total with taxes and fees
Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
$114 nightly
The price is $125
Apr 20 - Apr 21
Total with taxes and fees
Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
$119 nightly
The price is $131
Apr 21 - Apr 22
Total with taxes and fees
Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
$119 nightly
The price is $131
Apr 20 - Apr 21
Total with taxes and fees
Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
$114 nightly
The price is $125
Apr 27 - Apr 28
Total with taxes and fees
Sleep Woodstock - 2 Double Beds - Dog Friendly

Snowed Inn

Snowed Inn
3.5 star property
Killington
9.8 out of 10, Exceptional, (394 reviews)
"Wonderful stay"
United States
Gregory
$208 nightly
The price is $229
Apr 19 - Apr 20
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

Find out more about Windsor

Windsor B&B information

Number of reviews
1,106
Accommodation
38 B&B
Lowest Price
$125
Highest Price
$273

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 $125 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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