Cottages in Windsor County

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Check prices for these dates

In two weeks
10 Apr - 12 Apr
In two months
22 May - 24 May
In three months
19 Jun - 21 Jun
In four months
17 Jul - 19 Jul

Our top choices for Windsor County cottages

Exterior

Addie's Place: A Quiet and Quirky Guesthouse

Addie's Place: A Quiet and Quirky Guesthouse
Hartford
10.0 out of 10, Exceptional, (8 reviews)
"Perfect size and location! "
United States
Lyn H.
The price is AED 375
AED 722 total
includes taxes & fees
25 Mar - 26 Mar
Addie's Place: A Quiet and Quirky Guesthouse
Exterior

Woodstock Village Carriage House

Woodstock Village Carriage House
Woodstock
9.6 out of 10, Exceptional, (108 reviews)
"Clean, friendly host, quiet. Perfect location to everything in town"
United States
Mia M.
Woodstock Village Carriage House
Terrace/patio

Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit
Ludlow
9.4 out of 10, Exceptional, (22 reviews)
"Excellent location! Nicely renovated with great views of the lake. It could be a little hard to find in the dark on your first time there. There was a small issue with there, not being some towels in one of the bathrooms, but they did bring some by. Very nice place highly recommend!"
United States
Bruce B.
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit
Exterior

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
9.6 out of 10, Exceptional, (15 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!
House (4 Bedrooms) | Interior

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!
House (4 Bedrooms) | Interior

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!
Terrace/patio

Cozy Historic Hilltop Cottage with Mount Ascutney View

Cozy Historic Hilltop Cottage with Mount Ascutney View
West Windsor
9.6 out of 10, Exceptional, (84 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
House (5 Bedrooms) | Front of property

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!
Exterior

Terrific 3-bedroom cottage with AC in charming Cavendish

Terrific 3-bedroom cottage with AC in charming Cavendish
Cavendish
10.0 out of 10, Exceptional, (1 review)
"House was perfect! Well appointed with everything you need. Beds very comfortable and very clean. Host was very responsive and was there if you needed anything. Will definitely stay again. "
United States
Stephen S.
The price is AED 826
AED 2,230 total
includes taxes & fees
25 Mar - 26 Mar
Terrific 3-bedroom cottage with AC in charming Cavendish
House (2 Bedrooms) | Interior

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!
House (3 Bedrooms) | Interior

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!
House (2 Bedrooms) | Interior

Ludlow Ski Cabin 2 Mi to Ski Parking

Ludlow Ski Cabin 2 Mi to Ski Parking
3.0 star property
Ludlow
Ludlow Ski Cabin 2 Mi to Ski Parking
House (3 Bedrooms) | Interior

Killington Area Escape w/ Deck, Views & Hot Tub!

Killington Area Escape w/ Deck, Views & Hot Tub!
3.0 star property
Stockbridge
Killington Area Escape w/ Deck, Views & Hot Tub!
House (3 Bedrooms) | Interior

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!
House (3 Bedrooms) | Interior

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!
House (3 Bedrooms) | Interior

Inviting Vermont Home On Mount Ascutney!

Inviting Vermont Home On Mount Ascutney!
3.0 star property
Brownsville
Inviting Vermont Home On Mount Ascutney!
House (6 Bedrooms) | Interior

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!
House (3 Bedrooms) | Interior

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!
Exterior

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
House (3 Bedrooms) | Interior

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!
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

The Quechee Inn at Marshland Farm

The Quechee Inn at Marshland Farm

10/10 Excellent
"Rooms are nicely decorated & in a condition that is expected for a historic Inn. Updated bathrooms are nicely done with wonderful linens & toiletries. All staff was friendly& helpful. Location is great for exploring nearby attractions & the dinner food was excellent. "
Melanie 2-night trip
Posted 4 hours ago
The Quechee Inn at Marshland Farm