Guest Houses in Windsor County

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Top cities in Windsor County

A wooden covered bridge with a sign reading 'Slippery When Wet' and a sign above the entrance that says 'Michael's Bridge.'
Hotels

Woodstock

Woodstock

Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

Our top choices for Windsor County guest houses

A spacious room with a large bed, a sofa, and a chair, featuring large windows and a view of greenery outside.

1. Lincoln Inn & Gallery

Lincoln Inn & Gallery
3.0 star property
Woodstock
8.8 out of 10, Excellent, (121 reviews)
"The historic inn is so charming and relaxing. we love the location to town and the staff is so friendly. Luke, the owner, was very nice"
United States
Nhat Thuy
The price is CA $107
CA $118 total
includes taxes & fees
Nov 10 - Nov 11
Lincoln Inn & Gallery
A large building with a sloped roof, a covered entrance, and a grassy area in front.

2. Inn at Clearwater Pond (Quechee)

Inn at Clearwater Pond (Quechee)
3.5 star property
White River Junction
9.6 out of 10, Exceptional, (64 reviews)
"Tina is super friendly...great place to stay with the dogs!"
United States
Bryan
Inn at Clearwater Pond (Quechee)
A white two-story house with a front porch, a covered patio, and a well-maintained garden.

3. The Weston

The Weston
5.0 star property
Weston
9.6 out of 10, Exceptional, (15 reviews)
"The Weston is a spectacular small hotel. The restaurant is delicious and the staff go oabove and beyond to make your stay lovely."
United States
astrid
The price is CA $547
CA $596 total
includes taxes & fees
Nov 22 - Nov 23
The Weston
A kitchen with white cabinets, a wooden ceiling, and pendant lights.

4. Mountain cabin near skiing with fireplaces and A/C

Mountain cabin near skiing with fireplaces and A/C
Weston
9.8 out of 10, Exceptional, (14 reviews)
"Cute house, comfy bed, the surrounding area was so pretty. "
United States
Patrick M.
Mountain cabin near skiing with fireplaces and A/C
A modern kitchen with stainless steel appliances, a built-in oven, and a granite countertop.

5. Ludlow Village Guest House - prime location on ski shuttle, walk to restaurants

Ludlow Village Guest House - prime location on ski shuttle, walk to restaurants
Ludlow
9.8 out of 10, Exceptional, (44 reviews)
"We are repeat guests and really enjoyed our stay this time too. Super clean, centrally located place!"
United States
Jason S.
Ludlow Village Guest House - prime location on ski shuttle, walk to restaurants
A garden with a fire pit, Adirondack chairs, and a view of a green landscape.

6. Little House at Saskadena, right at the base of Ski Hill

Little House at Saskadena, right at the base of Ski Hill
Pomfret
10.0 out of 10, Exceptional, (1 review)
"Private and quiet and good location"
United States
Joyce Y.
Little House at Saskadena, right at the base of Ski Hill
A two-story house with a covered porch and a staircase leading to the upper level.

7. Victorian carriage house near skiing with deck and gas grill

Victorian carriage house near skiing with deck and gas grill
Ludlow
Victorian carriage house near skiing with deck and gas grill
A cozy living room with a fireplace, a sofa, a coffee table, and a dining area with chairs.

8. Cozy Vermont Ski Cottage | Near Killington

Cozy Vermont Ski Cottage | Near Killington
Bridgewater
Cozy Vermont Ski Cottage | Near Killington
A two-story building with a porch, a sign reading "Salt Ash Inn," and a smaller attached structure.

9. Salt Ash Inn

Salt Ash Inn
3.0 star property
Plymouth
6.2 out of 10, (126 reviews)
"Great place, close proximity to Killington. Clean & quiet...Recommend this location."
United States
Kingston F.
Salt Ash 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 reviews in Windsor County

A spacious room with a large bed, a sofa, and a chair, featuring large windows and a view of greenery outside.
Lincoln Inn & Gallery

Lincoln Inn & Gallery

Lincoln Inn & Gallery
Woodstock

10/10 Excellent

This is a really nice property with parking and a river across. It’s beautiful with a lot of outdoor space. Rooms were decent and staff was nice and helpful.
Canada
Simran
Reviewed September 15, 2026
Lincoln Inn & Gallery

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