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

Book Windsor Bed & Breakfast

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Our top choices for Windsor bed & breakfast

1. The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (323 reviews)
"Love staying in this beautiful hotel had very comfy beds and made us feel like we were in the heart of New England"
United States
Laura
$238 nightly
The price is $262
Nov 1 - Nov 2
Total with taxes and fees
The Jackson

2. The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (80 reviews)
"Room great breakfast fantastic Location a 10"
United States
Keith
$165 nightly
The price is $182
Oct 25 - Oct 26
Total with taxes and fees
The Vesper

3. Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (54 reviews)
"My husband kept saying that the room was a model for providing everything a traveler might need. Lovely stay."
United States
Jeanne
$299 nightly
The price is $329
Oct 29 - Oct 30
Total with taxes and fees
Stay At Jimmy's

4. Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
$214 nightly
The price is $236
Oct 29 - Oct 30
Total with taxes and fees
Sleep Woodstock - 2 Double Beds - Dog Friendly

5. 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
$220 nightly
The price is $242
Nov 1 - Nov 2
Total with taxes and fees
Deer Brook Inn

6. Woodbridge Inn

Woodbridge Inn
3.0 star property
Woodstock
9.6 out of 10, Exceptional, (68 reviews)
"Great place to stay"
United States
eric
$550 nightly
The price is $605
Oct 20 - Oct 21
Total with taxes and fees
Woodbridge Inn

7. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
$192 nightly
The price is $212
Oct 27 - Oct 28
Total with taxes and fees
Sleep Woodstock - Dog Friendly King Suite

8. 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.
$192 nightly
The price is $212
Oct 27 - Oct 28
Total with taxes and fees
Sleep Woodstock - Dog Friendly King Suite

9. Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
$170 nightly
The price is $188
Oct 27 - Oct 28
Total with taxes and fees
Sleep Woodstock - 2 Double Beds - Dog Friendly

10. Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
$170 nightly
The price is $188
Oct 27 - Oct 28
Total with taxes and fees
Sleep Woodstock - 2 Double Beds - Dog Friendly

11. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
$198 nightly
The price is $218
Oct 28 - Oct 29
Total with taxes and fees
Sleep Woodstock - Dog Friendly King Suite

12. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
$192 nightly
The price is $212
Oct 27 - Oct 28
Total with taxes and fees
Sleep Woodstock - Dog Friendly King Suite

13. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
$192 nightly
The price is $212
Oct 27 - Oct 28
Total with taxes and fees
Sleep Woodstock - Dog Friendly King Suite

14. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
$192 nightly
The price is $212
Oct 27 - Oct 28
Total with taxes and fees
Sleep Woodstock - Dog Friendly King Suite

15. Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
8.6 out of 10, Excellent, (104 reviews)
"Beautiful property! The charm and character of the place were amazing. Staff was friendly and very helpful. Rooms were quaint and well appointed, clean with comfy beds!"
United States
Amanda
$279 nightly
The price is $304
Oct 13 - Oct 14
Total with taxes and fees
Echo Lake Inn

16. Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (128 reviews)
"Wonderful staff and restaurant"
United States
John
$260 nightly
The price is $284
Oct 28 - Oct 29
Total with taxes and fees
Stone Hearth Inn and Eatery

17. Sleep Woodstock Mobility Impaired Accessible Suite

Sleep Woodstock Mobility Impaired Accessible Suite
Woodstock
$165 nightly
The price is $182
Oct 28 - Oct 29
Total with taxes and fees
Sleep Woodstock Mobility Impaired Accessible Suite

18. Snowed Inn

Snowed Inn
3.5 star property
Killington
9.8 out of 10, Exceptional, (415 reviews)
"Great hot tub and breakfast."
United States
Brendan
$152 nightly
The price is $167
Oct 25 - Oct 26
Total with taxes and fees
Snowed Inn

19. Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (287 reviews)
"Beautiful views of the river excellent breakfast"
United States
Michael
$169 nightly
The price is $184
Nov 1 - Nov 2
Total with taxes and fees
Harvest Barn 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
1,467
Accommodation
38 B&B
Lowest Price
$167
Highest Price
$605

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 $167 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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