A river flowing through a forest with autumn foliage.

B&B in Windsor County

Compare and save

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

Our top choices for Windsor County 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
The price is SAR 463
SAR 509 total
includes taxes & fees
8 Nov - 9 Nov
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, (80 reviews)
"Room great breakfast fantastic Location a 10"
United States
Keith
The price is SAR 620
SAR 682 total
includes taxes & fees
12 Nov - 13 Nov
The Vesper
A red barn with a white door and shutters, surrounded by a garden with various plants and flowers.

3. 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
The price is SAR 829
SAR 903 total
includes taxes & fees
13 Nov - 14 Nov
Stone Hearth Inn and Eatery
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, (7 reviews)
"Everything was fantastic, my room and the staff."
United States
Laurence
The price is SAR 874
SAR 961 total
includes taxes & fees
12 Nov - 13 Nov
Deer Brook Inn
A two-story house with a snow-covered yard and a well-lit front porch.

5. Golden Stage Inn B&B

Golden Stage Inn B&B
3.5 star property
Cavendish
10.0 out of 10, Exceptional, (47 reviews)
"The Golden Stage Inn was one of the highlights of our Vermont trip. Mike and Julie are wonderful hosts and have clearly put so much care into making the entire experience special. Our room was cozy, spacious, and beautifully kept, with a fireplace, lovely bathroom, and one of the most comfortable beds we’ve slept in while traveling. Breakfast alone is a reason to stay here. The two-course breakfasts were phenomenal, with fresh, local ingredients, juice, and plenty of coffee, all served in a...
United States
Andrew
Golden Stage Inn B&B
A large, multi-story building with a symmetrical facade, multiple windows, and a balcony with railings.

6. Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
8.8 out of 10, Excellent, (106 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
Echo Lake Inn
A modern fitness center with exercise equipment, mirrors, and a reception area.

7. 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
The price is SAR 1,123
SAR 1,235 total
includes taxes & fees
29 Oct - 30 Oct
Stay At Jimmy's
A modern living room with a sofa, chairs, a coffee table, a fireplace, and a kitchen area in the background.

8. Sleep Woodstock Mobility Impaired Accessible Suite

Sleep Woodstock Mobility Impaired Accessible Suite
Woodstock
The price is SAR 327
SAR 528 total
includes taxes & fees
10 Nov - 11 Nov
Sleep Woodstock Mobility Impaired Accessible 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
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.
The price is SAR 390
SAR 659 total
includes taxes & fees
9 Nov - 10 Nov
Sleep Woodstock - Dog Friendly King Suite
A house with a red roof, a porch with white railings, and a blue door.

10. Woodbridge Inn

Woodbridge Inn
3.0 star property
Woodstock
9.6 out of 10, Exceptional, (70 reviews)
The price is SAR 1,859
SAR 2,045 total
includes taxes & fees
20 Oct - 21 Oct
Woodbridge Inn
A row of cabins with a snow-covered ground and trees in the background.

11. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
Sleep Woodstock - Dog Friendly King Suite
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
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.
Sleep Woodstock - Dog Friendly King Suite
A man serving drinks at an outdoor table with a white tablecloth, surrounded by guests.

13. The Village Inn of Woodstock

The Village Inn of Woodstock
4.0 star property
Woodstock
9.6 out of 10, Exceptional, (103 reviews)
"Owners were very friendly. Food was incredible. Breakfast is included but they also have dinner available. Both were excellent. It was also nice having a small bar on site. Great place for a few drinks before we went out."
United States
Sam
The Village Inn of Woodstock
A white building with green shutters, a brick chimney, and a picket fence.

14. The Woodstocker B&B

The Woodstocker B&B
4.0 star property
Woodstock
10.0 out of 10, Exceptional, (53 reviews)
"This food at this property is amazing!! I would come back any day, the bread and entire menu is incredible. The zagat should try their breakfast! "
United States
Kavina
The Woodstocker B&B
A row of cabins with a snow-covered ground and trees in the background.

15. 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
Sleep Woodstock - Dog Friendly King Suite
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
8.0 out of 10, Very good, (1 review)
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
Sleep Woodstock - 2 Double Beds - Dog Friendly
A row of cabins with a snow-covered ground and trees in the background.

18. Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
Sleep Woodstock - 2 Double Beds - Dog Friendly
A row of cabins with a snow-covered ground and trees in the background.

19. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
Sleep Woodstock - Dog Friendly King Suite
A large, two-story building with a prominent entrance and steps leading up to it.

20. Windsor Mansion Inn

Windsor Mansion Inn
3.5 star property
Windsor
9.2 out of 10, Wonderful, (289 reviews)
"We had a lovely time at the Windsor Mansion Inn over New Years! Andy was incredible accommodating and friendly to make our group feel right at home. The beds were very comfortable the the rooms were spacious. The mansion is gorgeous. Yummy breakfast too. We hope to stay again!"
United States
Margaret
Windsor Mansion 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windsor County Hotel Reviews

Sleep Woodstock Motel

Sleep Woodstock Motel

10/10 Excellent
"An interesting hotel as the contact is all virtual. The room was a nice size, very clean and decorated really well. The common area was very clean, nice to have W/D for some travelers. My wife’s favorite stay of the six places we had on this leaf peeper road trip through VT and NH"
Lyle 1-night trip
Posted 3 hours ago
Sleep Woodstock Motel