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 wooden deck with a table and chairs overlooking a lake, surrounded by trees.

1. 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 3.854.928 ₫
7.721.757 ₫ total
includes taxes & fees
20 Oct - 21 Oct
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
A cabin with a porch, surrounded by a grassy yard and trees.

2. 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.

3. 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.

4. 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

5. 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.

6. 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.

7. 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 covered porch with a wooden ceiling, a dining table with chairs, a grill, and a view of trees.

8. 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.

9. 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.

10. 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.

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

All-season Lake House Between Okemo & Killington!
3.0 star property
Plymouth
All-season Lake House Between Okemo & Killington!
A wooden deck with Adirondack chairs and a table, overlooking a forested area.

12. 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.

13. Killington Cabin, Hot Tub & Foliage Views!

Killington Cabin, Hot Tub & Foliage Views!
3.0 star property
Stockbridge
Killington Cabin, Hot Tub & Foliage Views!
A log cabin with a wooden deck and a view of a forest.

14. Private Chester Home w/ Deck, Mins to Skiing!

Private Chester Home w/ Deck, Mins to Skiing!
3.0 star property
Chester
Private Chester Home w/ Deck, Mins to Skiing!
A wooden porch with a white railing, a covered area with a light fixture, and a view of a street with houses and trees.

15. 18 Mi to Skiing: Colorful Home in Springfield!

18 Mi to Skiing: Colorful Home in Springfield!
3.0 star property
Springfield
18 Mi to Skiing: Colorful Home in Springfield!
A blue house with a snow-covered roof and a garage door.

16. Vermont Retreat w/ Hot Tub: Romantic Getaway

Vermont Retreat w/ Hot Tub: Romantic Getaway
3.0 star property
Rochester
Vermont Retreat w/ Hot Tub: Romantic Getaway
A blue house with a balcony and a covered porch.

17. Weston Vacation Rental - Close to Ski Resorts!

Weston Vacation Rental - Close to Ski Resorts!
3.0 star property
Weston
Weston Vacation Rental - Close to Ski Resorts!
A house surrounded by dense forest with a clear path leading to the entrance.

18. Hike, Ski & Unwind: Cabin w/ Deck in Chester!

Hike, Ski & Unwind: Cabin w/ Deck in Chester!
3.0 star property
Chester
2.0 out of 10, (1 review)
Hike, Ski & Unwind: Cabin w/ Deck in Chester!
A white two-story house with a gabled roof, a front porch with two chairs, and a small garden area.

19. Ski Okemo! Hot Tub & Fireplace Ludlow Retreat

Ski Okemo! Hot Tub & Fireplace Ludlow Retreat
3.0 star property
Ludlow
Ski Okemo! Hot Tub & Fireplace Ludlow Retreat
A wooden deck with wicker furniture, a glass door, and a view of autumn trees.

20. Andover Cabin Retreat w/ Hot Tub & Fireplace!

Andover Cabin Retreat w/ Hot Tub & Fireplace!
3.0 star property
Chester
Andover Cabin Retreat w/ Hot Tub & Fireplace!
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

Align Inn Vermont

Align Inn Vermont

8/10 Good
"For the price it was a nice clean hotel"
Rafik 1-night trip
Posted less than an hour ago
Align Inn Vermont

Find out more about Windsor County

Windsor County Cottages information

Number of reviews
2
Accommodation
44 Cottages
Lowest Price
7.721.757 ₫
Highest Price
55.639.806 ₫