A river flowing through a forest with autumn foliage.

Cottages in Windsor County

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Windsor County cottages

A white house with a red roof and a hammock in the yard.

1. Addie's Place: A Quiet and Quirky Guesthouse

Addie's Place: A Quiet and Quirky Guesthouse
Hartford
9.6 out of 10, Exceptional, (19 reviews)
"Nice cottage setting in a quiet neighborhood, my dogs loved it!"
United States
Victor R.
The price is AED 477
AED 855 total
includes taxes & fees
27 Oct - 28 Oct
Addie's Place: A Quiet and Quirky Guesthouse
A two-story house with a snow-covered lawn, a wooden deck, and a garage.

2. Norwich Village cottage built 2026 2 miles to Dartmouth+King Arthur Baking Co.

Norwich Village cottage built 2026 2 miles to Dartmouth+King Arthur Baking Co.
Norwich
10.0 out of 10, Exceptional, (13 reviews)
"This is a wonderful place. Every detail is perfectly considered and the property is immaculate and extremely well appointed. The hosts are gracious and considerate. Great location. Will absolutely be back. Highly recommended!"
United States
Rob P.
Norwich Village cottage built 2026 2 miles to Dartmouth+King Arthur Baking Co.
A two-story house with a garage, a small porch, and a chimney.

3. Woodstock Village Carriage House

Woodstock Village Carriage House
Woodstock
9.6 out of 10, Exceptional, (117 reviews)
"The carriage house had everything we needed for our visit. It was perfect and would definitely stay here again."
United States
anthony
Woodstock Village Carriage House
A deck with a metal chair and a decorative vase, overlooking a forested area with autumn foliage.

4. Cozy Historic Hilltop Cottage with Mount Ascutney View

Cozy Historic Hilltop Cottage with Mount Ascutney View
West Windsor
9.6 out of 10, Exceptional, (88 reviews)
"Beautiful country! Very laid back atmosphere!Easy to check in and out. Great experience!"
United States
Paul H.
Cozy Historic Hilltop Cottage with Mount Ascutney View
A red building with a black door, surrounded by a gravel driveway and a wooden fence.

5. Cozy cottage on the river, minutes from skiing, horse events, and so much more!

Cozy cottage on the river, minutes from skiing, horse events, and so much more!
Reading
9.8 out of 10, Exceptional, (22 reviews)
"We loved the place and will stay again"
United States
Michelle
Cozy cottage on the river, minutes from skiing, horse events, and so much more!
A two-story house with a covered porch, surrounded by a well-maintained lawn and trees.

6. Renovated Vermont Retreat with mountain views near Okemo & Killington for 8

Renovated Vermont Retreat with mountain views near Okemo & Killington for 8
Cavendish
10.0 out of 10, Exceptional, (2 reviews)
"Such a beautiful place and we loved the area. It was our first trip to Vermont. "
United States
Mark G.
The price is AED 654
AED 1,987 total
includes taxes & fees
4 Nov - 5 Nov
Renovated Vermont Retreat with mountain views near Okemo & Killington for 8
A wooden deck with a table and chairs overlooking a lake, surrounded by trees.

7. Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit

Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
3.0 star property
Ludlow
The price is AED 547
AED 1,096 total
includes taxes & fees
15 Oct - 16 Oct
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
A cabin with a porch, surrounded by a grassy yard and trees.

8. Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!

Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!
3.0 star property
Chester
10.0 out of 10, Exceptional, (2 reviews)
"The property was lovely, peaceful, and quiet, surrounded by trees on a quiet country drive. It was the perfect weekend getaway and we really enjoyed sitting on the porch and out under the string lights, watching the sun go down through the trees. The house itself is lovely, cozy, and comfortable. Our hosts were very sweet, everything was very thoughtfully laid out and clean and easy to access. We also loved meeting the goats, Ozzy and Coco, and the chickens! This was such a pleasant stay, I...
United States
Angela
Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!
A cabin with a wooden deck, large windows, and a chimney.

9. Family-friendly Ludlow Cabin on Lake Pauline!

Family-friendly Ludlow Cabin on Lake Pauline!
3.0 star property
Ludlow
Family-friendly Ludlow Cabin on Lake Pauline!
A wooden deck with white railings, a view of houses, and a clear sky.

10. Lovely Ludlow Farmhouse ~ 1 Mi to Town & Slopes!

Lovely Ludlow Farmhouse ~ 1 Mi to Town & Slopes!
3.0 star property
Ludlow
10.0 out of 10, Exceptional, (1 review)
"Great place "
United States
Mauro
Lovely Ludlow Farmhouse ~ 1 Mi to Town & Slopes!
Interior

11. Picture-perfect Vermont Mtn Cabin w/ Hot Tub!

Picture-perfect Vermont Mtn Cabin w/ Hot Tub!
3.0 star property
Bridgewater Corners
Picture-perfect Vermont Mtn Cabin w/ Hot Tub!
A rustic cabin with a large barn, surrounded by a pond and dense forest.

12. Chester Farmhouse on 100 Acres, 15 Min to Okemo!

Chester Farmhouse on 100 Acres, 15 Min to Okemo!
3.0 star property
Chester
Chester Farmhouse on 100 Acres, 15 Min to Okemo!
A wooden deck with Adirondack chairs and a glass door leading to a mountain view.

13. Luxury Vermont Vacation Rental: Private Hot Tub!

Luxury Vermont Vacation Rental: Private Hot Tub!
3.0 star property
Brownsville
Luxury Vermont Vacation Rental: Private Hot Tub!
A house with a covered porch, a fire pit with chairs, and string lights.

14. 4bdrm Cottage central to year round fun w/fireplace

4bdrm Cottage central to year round fun w/fireplace
Weston
4bdrm Cottage central to year round fun w/fireplace
A covered porch with a wooden ceiling, a dining table with chairs, a grill, and a view of trees.

15. Peaceful Cavendish Retreat w/ Hot Tub & Fireplace!

Peaceful Cavendish Retreat w/ Hot Tub & Fireplace!
3.0 star property
Cavendish
Peaceful Cavendish Retreat w/ Hot Tub & Fireplace!
A modern house with a stone pathway leading to the entrance, surrounded by a forest.

16. Resort-style Community! Quechee Chalet w/ Deck

Resort-style Community! Quechee Chalet w/ Deck
3.0 star property
Quechee
Resort-style Community! Quechee Chalet w/ Deck
A red two-story house with a balcony, a picnic table, and an umbrella in a lush green backyard.

17. Inviting Vermont Home On Mount Ascutney!

Inviting Vermont Home On Mount Ascutney!
3.0 star property
Brownsville
Inviting Vermont Home On Mount Ascutney!
A deck with a round table and chairs, a fire pit, and a hanging flower basket.

18. All-season Lake House Between Okemo & Killington!

All-season Lake House Between Okemo & Killington!
3.0 star property
Plymouth
10.0 out of 10, Exceptional, (1 review)
"House is amazing,beautiful location,definitely we will go back. Host very friendly."
United States
Sandra
All-season Lake House Between Okemo & Killington!
A wooden deck with Adirondack chairs and a table, overlooking a forested area.

19. 8 Mi to Okemo Mountain Resort: Mtn-view Retreat!

8 Mi to Okemo Mountain Resort: Mtn-view Retreat!
3.0 star property
Ludlow
10.0 out of 10, Exceptional, (1 review)
"Everything was as advertised we had an ice storm and a nice guy came and salted stairs and driveway bright an early , the only issue we has was the inside steps going to the upstairs bedroom were very slippery but otherwise great stay "
United States
JIM
8 Mi to Okemo Mountain Resort: Mtn-view Retreat!
A wooden deck with a hot tub, outdoor seating, and a view of a forested hillside.

20. Killington Cabin, Hot Tub & Foliage Views!

Killington Cabin, Hot Tub & Foliage Views!
3.0 star property
Stockbridge
Killington Cabin, Hot Tub & Foliage Views!
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 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 7 hours ago
Sleep Woodstock Motel

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