Photo by William E Berry Jr.

Search Windsor Cottage Rentals from CA $264

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Browse Select Windsor Cottages

Cozy Crescent Cottage

10.0 out of 10, Exceptional, (25)
"We had a wonderful long weekend stay at the cottage on Crescent Lake! The place has all of the amenities that you need for a relaxing and fun filled time on the lake. We will definitely be back for another stay next year!"
Cozy Crescent Cottage

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

9.8 out of 10, Exceptional, (11)
"We loved the location and home! So close to Okemo, beautiful home right on the lake. The hottub and gas fireplace were appreciated after a day of skiing. We would definitely come back again!"
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

Cozy 1850s home on the riverfront with mountain & river views - dog-friendly

9.4 out of 10, Exceptional, (16)
"We loved the cabin and its proximity to the town of Woodstock. Nice to come home at the end of the day. The only issue is the bedrooms are upstairs and the bathroom is downstairs….but we managed. Overall a great stay. "
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly

Brook Road Cabin

3.5 star property
7.8 out of 10, Good, (9)
"In the aftermath of 30+” of snow we dug out and sought a new location with power and hot showers. How blessed we were to find this gem. A point of refuge and some much needed R&R. Cabin was quaint, warm, and comfortable, and the host was attentive and welcoming. Thank you for this port in the storm. 😊"
The price is CA $264
CA $425 total
includes taxes & fees
May 1 - May 2
Brook Road Cabin

Historic Hanover Area Home, 16 Miles to Dartmouth!

3.0 star property
10.0 out of 10, Exceptional, (1)
Historic Hanover Area Home, 16 Miles to Dartmouth!

Woodstock Village Carriage House

9.6 out of 10, Exceptional, (90)
"We loved the carriage house and its proximity to the town of Woodstock. Perfect to come home at the end of the day. Would definitely recommend to anyone visiting Woodstock! "
Woodstock Village Carriage House

Sweet vintage cottage on Mountain View Lake, 2024 updates, next to Lake Sunapee

Sweet vintage cottage on Mountain View Lake, 2024 updates, next to Lake Sunapee

Cozy Historic Hilltop Cottage with Mount Ascutney View

9.8 out of 10, Exceptional, (76)
"Had a great stay at the old school house. Location was perfect for what we needed. Place was super clean and well appointed. Would love to come back again."
Cozy Historic Hilltop Cottage with Mount Ascutney View

The Cairn, 1840s Cozy Stone Cottage, Pet Friendly

10.0 out of 10, Exceptional, (11)
"We very much enjoyed our stay in this historic, architecturally significant home. We would definitely stay here again."
The Cairn, 1840s Cozy Stone Cottage, Pet Friendly

Ski-Hike-Relax! Remodeled cottage with White River access in the Green Mountains

10.0 out of 10, Exceptional, (9)
"If you’re looking to spend a weekend with some friends at Killington this is definitely the most bang for your buck outside of the resort. 20 minute drive and plenty of plowed parking. "
Ski-Hike-Relax! Remodeled cottage with White River access in the Green Mountains

Lovely Ludlow Farmhouse ~ 1 Mi to Town & Slopes!

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

Pet-friendly Claremont Vacation Rental!

3.0 star property
Pet-friendly Claremont Vacation Rental!

Lakeside life at its best!

9.8 out of 10, Exceptional, (47)
"My family of four traveled for a quick fall foliage tour mid October. We used this house as our base instead of staying at multiple places. This meant we drove a little more each day but we got to wake up and come home to this magical place. Seriously. We wanted to come home early each day to spend more time here. It’s quiet, enchanting, spotless, and filled with charm. I cannot stress how beautiful and peaceful it is being directly on the lake. We will definitely be back. "
Lakeside life at its best!

Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!

3.0 star property
Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!

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

10.0 out of 10, Exceptional, (7)
"very good cozy location. enjoyed the privacy during our stay."
Cozy cottage on the river, minutes from skiing, horse events, and so much more!

Weston Vacation Rental - Close to Ski Resorts!

3.0 star property
Weston Vacation Rental - Close to Ski Resorts!

Picture-perfect Vermont Mtn Cabin w/ Hot Tub!

3.0 star property
Picture-perfect Vermont Mtn Cabin w/ Hot Tub!

4bdrm Cottage central to year round fun w/fireplace

4bdrm Cottage central to year round fun w/fireplace

Spruce Moose Cottage | Tiny House on 65 private acres

Spruce Moose Cottage | Tiny House on 65 private acres

18 Mi to Skiing: Colorful Home in Springfield!

3.0 star property
18 Mi to Skiing: Colorful Home in Springfield!
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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Other property types in Windsor

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (42)
"Very nice place only negative was the sauna did not work"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Cozy Crescent Cottage

10.0 out of 10, Exceptional, (25)
"We had a wonderful long weekend stay at the cottage on Crescent Lake! The place has all of the amenities that you need for a relaxing and fun filled time on the lake. We will definitely be back for another stay next year!"
Cozy Crescent Cottage

Beautifully renovated with fireplace and coffee bar

10.0 out of 10, Exceptional, (103)
"We had a great winter weekend! The accommodations were just what we needed, perfect location and the coffee bar was amazing! We cant wait to come back again!"
Beautifully renovated with fireplace and coffee bar
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.