Photo by William E Berry Jr.

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Compare 77 Cottages in Windsor with updated reviews, rates, and availability.

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

Cozy Crescent Cottage

10.0 out of 10, Exceptional, (25)
"This was our second stay at the cozy cottage amd was just as enjoyable as the first time . Glenn and Melanie are very responsive and like to makesure their guests are comfortable and happy . We loved waking up on the lake and enjoyed the back deck and firepit. We look forward to renting here again in the future. P"
Cozy Crescent Cottage

Brook Road Cabin

3.5 star property
7.8 out of 10, Good, (9)
"This little cabin is exactly what the owner purports it to be. No more; no less. It's quaint and the bedrooms are small. Because it's a cabin. The shower is small. Because it's a cabin. The TV and stove and sink are all small. Because it's a cabin! There are a few ants around, but there's Raid spray under the sink if you want to go that route. The occasional ant is going to show it's occasional self. It's a cabin. in the woods... I thought it was a fair accommodation for a fair price (just a...
The price is SAR 645
SAR 1,074 total
includes taxes & fees
24 Mar - 25 Mar
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

New Lakeside Cottage near Okemo and Killington

9.6 out of 10, Exceptional, (153)
"We had an amazing week swimming, hiking, paddling, and admiring gorgeous Lake Amherst. All of our favorite things were nearby - lovely hiking trails, and maple ice cream. Perfect location, well appointed kitchen, and perfect dock on the lake. Our family loved every moment and we hope to come back again."
New Lakeside Cottage near Okemo and Killington

Cozy Historic Hilltop Cottage with Mount Ascutney View

9.8 out of 10, Exceptional, (76)
"This was the perfect cottage for a winter getaway. I was solo, but the home could have easily accommodated many more. I loved the vintage touches and had a nice time listening to the classic vinyl records while enjoying a glass of wine and watching it snow. I had dinner outside on the patio one night and the view was lovely. It is just a few minutes drive from Woodstock and Quechee and I visited both several times. The cottage was clean and had everything I needed. Highly recommend for a quiet,...
Cozy Historic Hilltop Cottage with Mount Ascutney View

The Cairn, 1840s Cozy Stone Cottage, Pet Friendly

10.0 out of 10, Exceptional, (10)
"We started 2 nights while skiing at Okemo. It was a nice warm cozy spot to relax at the end of the day. Loved that it's a historic stone structure as well. Not to mention the covered bridge that you drive through on the way! "
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

Charming Cavendish Cottage: All-Season Retreat for fun and relaxation!

8.0 out of 10, Very Good, (1)
"Beautiful house with lots of very thoughtful amenities. Very clear and easy communication from owners as well. Great location for skiing Okemo and it was a lovely place to come back to after a day on the slopes. One issue was that the listing states this is a 4 bedroom home, but in fact there are only 3. This made for a tight squeeze for 5 adults (none of whom were couples). I'm wondering if this might have been a glitch on the website. We had a great stay, but had we known it was only 3...
Charming Cavendish Cottage: All-Season Retreat for fun and relaxation!

Pet-friendly Claremont Vacation Rental!

3.0 star property
Pet-friendly Claremont Vacation Rental!

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!

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!

18 Mi to Skiing: Colorful Home in Springfield!

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

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

10.0 out of 10, Exceptional, (7)
"We loved our stay at the Dark Horse Cottage. It was close to everything we wanted to do. We loved being near the little creek. They thought of everything for amenities. It was perfect for what we needed. "
Cozy cottage on the river, minutes from skiing, horse events, and so much more!

Newbury Family Getaway: Walk to Lake Sunapee

3.0 star property
10.0 out of 10, Exceptional, (1)
"We met some problems during our trip but the owner did his best to solve it . We appreicate it. The location of this house is very good, walk to lake and 10 mins to Sunappe mountain."
Newbury Family Getaway: Walk to Lake Sunapee

Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!

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

Wooded Waterfront Grantham Home < 10 Mi to Ski!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Great atmosphere!"
Wooded Waterfront Grantham Home < 10 Mi to Ski!

Weston Vacation Rental - Close to Ski Resorts!

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

Mountain Green

2.0 star property
5.8 out of 10, (8)
"The condo was very cozy for a family of four and suited us perfectly. Beds were comfortable and condo was clean. "
The price is SAR 765
SAR 1,026 total
includes taxes & fees
3 Apr - 4 Apr
Mountain Green

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (41)
"very clean and easy to access close to mountain"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

9.6 out of 10, Exceptional, (155)
"Two friends and I stayed at this house for the second year in a row. It has been a perfect place for us, being 10 minutes away from Grafton and 25 minutes from Okemo."
The price is SAR 638
SAR 1,349 total
includes taxes & fees
24 Mar - 25 Mar
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
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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