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

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  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1
In one month
Nov 13 - Nov 15
In two months
Dec 11 - Dec 13

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, (331 reviews)
"Amazing stay and great restaurant!"
United States
Ava
$176 nightly
The price is $194
Nov 5 - Nov 6
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, (81 reviews)
"Room great breakfast fantastic Location a 10"
United States
Keith
$165 nightly
The price is $182
Nov 9 - Nov 10
Total with taxes and fees
The Vesper
A modern fitness center with exercise equipment, mirrors, and a reception area.

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
A cozy living room with a fireplace, wicker chairs, and a coffee table with snacks.

4. Deer Brook Inn

Deer Brook Inn
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (8 reviews)
"Everything was fantastic, my room and the staff."
United States
Laurence
$212 nightly
The price is $233
Nov 1 - Nov 2
Total with taxes and fees
Deer Brook Inn
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.
$159 nightly
The price is $175
Oct 27 - Oct 28
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.

6. Woodbridge Inn

Woodbridge Inn
3.0 star property
Woodstock
9.6 out of 10, Exceptional, (70 reviews)
"We loved our stay here. Everyone was so nice. The beds were incredibly comfortable. We arrived in the late afternoon in time for happy hour. We sat outside near the fire pit and watched the sunset behind the mountains. It’s a little outside of Woodstock but very convenient."
United States
Michelle
$550 nightly
The price is $605
Oct 20 - Oct 21
Total with taxes and fees
Woodbridge Inn
A row of cabins with a snow-covered ground and trees in the background.

7. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
10.0 out of 10, Exceptional, (1 review)
"Our stay at this property was a pleasant surprise. Room was spotless and provided everything we needed. Bed was super comfortable and the location was perfect. There is a bit of road noise during the day but none at all at night. Would highly recommend this property."
United States
Mark & Joan S.
$159 nightly
The price is $175
Nov 9 - Nov 10
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.

8. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
8.0 out of 10, Very good, (1 review)
"Old but nice and clean."
United States
James
$159 nightly
The price is $175
Nov 9 - Nov 10
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.

9. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
8.0 out of 10, Very good, (1 review)
$159 nightly
The price is $175
Nov 16 - Nov 17
Total with taxes and fees
Sleep Woodstock - Dog Friendly King Suite
A modern living room with a sofa, chairs, a coffee table, a fireplace, and a kitchen area in the background.

10. Sleep Woodstock Mobility Impaired Accessible Suite

Sleep Woodstock Mobility Impaired Accessible Suite
Woodstock
$119 nightly
The price is $131
Nov 16 - Nov 17
Total with taxes and fees
Sleep Woodstock Mobility Impaired Accessible Suite
A row of cabins with a snow-covered ground and trees in the background.

11. Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
$159 nightly
The price is $175
Nov 9 - Nov 10
Total with taxes and fees
Sleep Woodstock - 2 Double Beds - Dog Friendly
A row of cabins with a snow-covered ground and trees in the background.

12. Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
$159 nightly
The price is $175
Oct 27 - Oct 28
Total with taxes and fees
Sleep Woodstock - 2 Double Beds - Dog Friendly
A bathroom with a sink, mirror, vanity, towel rack, and a toilet.

13. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
$159 nightly
The price is $175
Nov 9 - Nov 10
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 - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
$159 nightly
The price is $175
Oct 27 - Oct 28
Total with taxes and fees
Sleep Woodstock - 2 Double Beds - Dog Friendly
A row of cabins with a snow-covered ground and trees in the background.

15. Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
$148 nightly
The price is $164
Oct 20 - Oct 21
Total with taxes and fees
Sleep Woodstock - 2 Double Beds - Dog Friendly
A row of cabins with a snow-covered ground and trees in the background.

16. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
$159 nightly
The price is $175
Nov 9 - Nov 10
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.

17. Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
$159 nightly
The price is $175
Oct 27 - Oct 28
Total with taxes and fees
Sleep Woodstock - 2 Double Beds - Dog Friendly
A rustic room with a ping pong table, wooden walls, and a ceiling fan.

18. 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
$233 nightly
The price is $252
Nov 8 - Nov 9
Total with taxes and fees
Dexter's Inn
A red barn with a white door and shutters, surrounded by a garden with various plants and flowers.

19. Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (130 reviews)
"Wonderful staff and restaurant"
United States
John
$193 nightly
The price is $210
Nov 16 - Nov 17
Total with taxes and fees
Stone Hearth Inn and Eatery
A wooden-paneled bedroom with a bed, a nightstand with a lamp, and a window with curtains.

20. Snowed Inn

Snowed Inn
3.5 star property
Killington
9.8 out of 10, Exceptional, (423 reviews)
"A+ stay, everything was great about our stay here"
United States
Melissa
$140 nightly
The price is $154
Oct 25 - Oct 26
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

Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

10/10 Excellent
"Beautiful place"
Amber 1-night trip
Posted less than an hour ago
Jackson Gore Village, A Vail Resorts Property

Find out more about Windsor

Windsor B&B information

Number of reviews
839
Accommodation
36 B&B
Lowest Price
$131
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 $131 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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