Top B&B in Windsor County in 2026

A river flowing through a forest with autumn foliage.

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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

West Woodstock

Brian

RM794 total

includes taxes & fees

30 Aug - 31 Aug

A living room with a grey sectional sofa, a potted plant, and a radiator.

2. The Vesper

Woodstock

Keith

RM776 total

includes taxes & fees

31 Aug - 1 Sept

A modern fitness center with exercise equipment, mirrors, and a reception area.

3. Stay At Jimmy's

Woodstock

Heather

RM1,546 total

includes taxes & fees

15 Sept - 16 Sept

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

4. Deer Brook Inn

Woodstock

Laurence

RM1,032 total

includes taxes & fees

30 Aug - 31 Aug

A red barn with a white door and shutters, surrounded by a garden with various plants and flowers.

5. Stone Hearth Inn and Eatery

Chester

Olena

RM917 total

includes taxes & fees

10 Sept - 11 Sept

A large, multi-story building with a symmetrical facade, multiple windows, and a balcony with railings.

6. Echo Lake Inn

Plymouth

Michael

RM1,013 total

includes taxes & fees

1 Sept - 2 Sept

A man serving drinks at an outdoor table with a white tablecloth, surrounded by guests.

7. The Village Inn of Woodstock

Woodstock

Sam

A house with a red roof, a porch with white railings, and a blue door.

8. Woodbridge Inn

Woodstock

eric

RM2,196 total

includes taxes & fees

7 Sept - 8 Sept

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Top Windsor County Hotel Reviews

On The River Inn

10/10 Excellent

"This place was set up even better than I expected. With nature right outside the door, it was so relaxing and stress-free, and the overall atmosphere was elegant and beautiful. Staff members are very friendly, too. The only thing was that the mattress was a bit too soft, which gave me a backache."

The Quechee Inn at Marshland Farm

10/10 Excellent

"Our stay was wonderful. Staff greeted us with a friendly hello and checked us in while explaining all we needed to know about our room and the property. Room was well appointed and very clean and comfortable. We especially enjoyed visiting with friends on the upstairs porch in the evening. Breakfast was amazing! Resort quality as opposed to the hotel breakfasts we experienced on the rest of our trip. We can’t wait to return."

The Shire Woodstock

8/10 Good

"We enjoyed our stay very much. We found our stay to very quiet. The back of the property was so peaceful and relaxing sitting by the river, listening to the birds and the gurgling of the river as it moves along. The room was comfortable with a fridge and freezer for snacks/fruit etc. I'd like to see another chair in the room so that 2 people can sit by the window and experience the view although this wasn't a game changer."

Deer Brook Inn

10/10 Excellent

"What an amazing place! The room was perfect--comfy bed, luxurious bedding and great amenities. As a guest, you have full access to the living room, dining room and outdoor areas--which includes a fire pit and sauna. Breakfast was delicious with locally sourced products--many from the property itself--including edible flowers. The host was friendly, welcoming, and just a delightful person. And so very thoughtful. Would definitely stay here again and highly recommend!"

The Hartness House

10/10 Excellent

"The historic property was beautifully landscaped and maintained from the front lawn and parking to the features in the back yard, including short shaded woodland trails. The interior of the historic home was lovely, clean, and welcoming with ample seating and window views, tea, coffee, etc., and snacks. The most comforting aspect of our stay was the hostess, sharing the history of the property and former owners, and offering a tour. The hostess and staff were sincere, kind and so helpful! I intend to stay at this place again!"

Find out more about Windsor County

Windsor County B&B information

Number of reviews	1,076
Accommodation	12 B&B
Lowest Price	RM776
Highest Price	RM2,196

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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Windsor County bed & breakfast

1. The Jackson

2. The Vesper

3. Stay At Jimmy's

4. Deer Brook Inn

5. Stone Hearth Inn and Eatery

6. Echo Lake Inn

7. The Village Inn of Woodstock

8. Woodbridge Inn

9. Golden Stage Inn B&B

10. The Woodstocker B&B

11. Windsor Mansion Inn

12. Inn at Water's Edge

Top Windsor County Hotel Reviews

On The River Inn

Align Inn Vermont

The Quechee Inn at Marshland Farm

The Shire Woodstock

Deer Brook Inn

Sleep Woodstock Motel

Lincoln Inn & Gallery

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

The Hartness House

Find out more about Windsor County

Windsor County B&B information

Explore a world of travel with Expedia