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

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

Check prices for these dates

Next weekend
Oct 2 - Oct 4
In two weeks
Oct 9 - Oct 11
In one month
Oct 23 - Oct 25
In two months
Nov 20 - Nov 22

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, (322 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
$451 nightly
The price is $496
Sep 27 - Sep 28
Total with taxes and fees
The Jackson
A red barn with a white door and shutters, surrounded by a garden with various plants and flowers.

2. Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (126 reviews)
"Wonderful staff and restaurant"
United States
John
$230 nightly
The price is $251
Sep 24 - Sep 25
Total with taxes and fees
Stone Hearth Inn and Eatery
A row of cabins with a snow-covered ground and trees in the background.

3. Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
$150 nightly
The price is $165
Sep 27 - Sep 28
Total with taxes and fees
Sleep Woodstock - 2 Double Beds - Dog Friendly
A living room with a grey sectional sofa, a potted plant, and a radiator.

4. The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (78 reviews)
"Room great breakfast fantastic Location a 10"
United States
Keith
$344 nightly
The price is $378
Oct 21 - Oct 22
Total with taxes and fees
The Vesper
A large, multi-story building with a symmetrical facade, multiple windows, and a balcony with railings.

5. Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
8.6 out of 10, Excellent, (103 reviews)
"Kat and everyone were very friendly and helpful, we had a wonderful stay"
United States
Michael
$289 nightly
The price is $315
Oct 13 - Oct 14
Total with taxes and fees
Echo Lake Inn
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, (67 reviews)
"Great place to stay"
United States
eric
$550 nightly
The price is $605
Sep 27 - Sep 28
Total with taxes and fees
Woodbridge Inn
A room with a large window overlooking a lake and forested hills. There are two wooden chairs on a balcony.

7. Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (282 reviews)
"Beautiful views of the river excellent breakfast"
United States
Michael
$188 nightly
The price is $205
Sep 24 - Sep 25
Total with taxes and fees
Harvest Barn Inn
A cozy living room with a fireplace, wicker chairs, and a coffee table with snacks.

8. 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
$392 nightly
The price is $432
Oct 24 - Oct 25
Total with taxes and fees
Deer Brook 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

Woodstock Inn & Resort

Woodstock Inn & Resort

10/10 Excellent
"Wonderful inn! Everything was wonderful: rooms, food, etc!!"
Ann 2-night trip
Posted 10 hours ago
Woodstock Inn & Resort

Find out more about Windsor

Windsor B&B information

Number of reviews
918
Accommodation
38 B&B
Lowest Price
$165
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 $165 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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