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

Book Windsor Bed & Breakfast

Check prices for these dates

Next weekend
Sep 11 - Sep 13
In two weeks
Sep 18 - Sep 20
In one month
Oct 2 - Oct 4
In two months
Oct 30 - Nov 1

Our top choices for Windsor bed & breakfast

A spacious room with a stone fireplace, leather furniture, and large windows offering a view of greenery.

1. The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (311 reviews)
"Everything was terrific! Great vibe & location."
United States
Brian
$166 nightly
The price is $182
Sep 8 - Sep 9
Total with taxes and fees
The Jackson
A living room with a grey sectional sofa, a potted plant, and a radiator.

2. The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (74 reviews)
"Room great breakfast fantastic Location a 10"
United States
Keith
$175 nightly
The price is $193
Sep 7 - Sep 8
Total with taxes and fees
The Vesper
A room with a large window overlooking a lake and forested hills. There are two wooden chairs on a balcony.

3. Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (277 reviews)
"Beautiful views of the river excellent breakfast"
United States
Michael
$172 nightly
The price is $187
Sep 2 - Sep 3
Total with taxes and fees
Harvest Barn Inn
A red barn with a white door and shutters, surrounded by a garden with various plants and flowers.

4. Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (123 reviews)
"We had a lovely stay at Stone Hearth Inn! Very quaint place and comfortable, clean accommodations. Beautiful grounds around the property with outside seating to enjoy the fresh air. The dinner we had at the attached “Eatery” was awesome!!! So was the amazingly delicious included breakfast. Vickie was so welcoming and kind. We can’t say enough good things! Highly recommend"
United States
Kathleen
$205 nightly
The price is $223
Sep 16 - Sep 17
Total with taxes and fees
Stone Hearth Inn and Eatery
A row of cabins with a snow-covered ground and trees in the background.

5. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
10.0 out of 10, Exceptional, (1 review)
"Considering the place was hit by a TORNADO the week prior to our visit, the accommodations were great, and the owner/host was in remarkably good spirits despite hassles with insurance."
United States
David M.
$144 nightly
The price is $159
Sep 7 - Sep 8
Total with taxes and fees
Sleep Woodstock - Dog Friendly King Suite
A cozy living room with a fireplace, wicker chairs, and a coffee table with snacks.

6. Deer Brook Inn

Deer Brook Inn
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (7 reviews)
"Everything was fantastic, my room and the staff."
United States
Laurence
$256 nightly
The price is $282
Sep 2 - Sep 3
Total with taxes and fees
Deer Brook Inn
A large, multi-story building with a symmetrical facade, multiple windows, and a balcony with railings.

7. Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
8.6 out of 10, Excellent, (101 reviews)
"Kat and everyone were very friendly and helpful, we had a wonderful stay"
United States
Michael
$204 nightly
The price is $222
Sep 16 - Sep 17
Total with taxes and fees
Echo Lake Inn
A modern fitness center with exercise equipment, mirrors, and a reception area.

8. Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (51 reviews)
"My husband kept saying that the room was a model for providing everything a traveler might need. Lovely stay."
United States
Jeanne
$349 nightly
The price is $384
Sep 10 - Sep 11
Total with taxes and fees
Stay At Jimmy's
A large, stone and wood lodge with a sign reading 'The Snowed Inn,' surrounded by snow-covered trees and a snow-covered driveway.

9. Snowed Inn

Snowed Inn
3.5 star property
Killington
9.8 out of 10, Exceptional, (406 reviews)
"Super clean hotel/ b&b that was perfect for my wife and I. Would stay again in a second. The staff went beyond expectations, Thanks!"
United States
James
$140 nightly
The price is $154
Sep 9 - Sep 10
Total with taxes and fees
Snowed Inn
A row of cabins with a snow-covered ground and trees in the background.

10. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
$144 nightly
The price is $159
Sep 7 - Sep 8
Total with taxes and fees
Sleep Woodstock - Dog Friendly King Suite
A house with a red roof, a porch with white railings, and a blue door.

11. Woodbridge Inn

Woodbridge Inn
3.0 star property
Woodstock
9.6 out of 10, Exceptional, (67 reviews)
"Great place to stay"
United States
eric
$495 nightly
The price is $545
Sep 16 - Sep 17
Total with taxes and fees
Woodbridge Inn
A row of cabins with a snow-covered ground and trees in the background.

12. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
$144 nightly
The price is $159
Sep 7 - Sep 8
Total with taxes and fees
Sleep Woodstock - Dog Friendly King Suite
A row of cabins with a snow-covered ground and trees in the background.

13. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
$150 nightly
The price is $165
Sep 7 - Sep 8
Total with taxes and fees
Sleep Woodstock - Dog Friendly King Suite
A row of cabins with a snow-covered ground and trees in the background.

14. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
$182 nightly
The price is $201
Sep 17 - Sep 18
Total with taxes and fees
Sleep Woodstock - Dog Friendly King Suite
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

On The River Inn

On The River Inn

10/10 Excellent
"We had a wonderful stay at On the River. The room was large, clean, and very quiet. It's a short, quick drive into town. The staff was pleasant and helpful. A good choice when staying near Woodstock."
Marc 1-night trip
Posted 3 hours ago
On The River Inn

Find out more about Windsor

Windsor B&B information

Number of reviews
1,277
Accommodation
38 B&B
Lowest Price
$154
Highest Price
$545

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 $154 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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