Photo by William E Berry Jr.

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Compare 68 Cottages in Windsor with updated reviews, rates, and availability.

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

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

10.0 out of 10, Exceptional, (7)
"Obsessed with this house! It was perfect for 2 couples and our pups for a relaxing fall weekend. Rooms were cozy, updated and super clean. The hot tub, fire pit by the river and big kitchen were highlights. I really appreciated the hospitality of having amenities like spices, coffee filters, shampoo & conditioner, laundry detergent, etc. Would book again!"
Ski-Hike-Relax! Remodeled cottage with White River access in the Green Mountains
Brook Road Cabin
Exterior

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 766
SAR 1,145 total
includes taxes & fees
23 Dec - 24 Dec
Brook Road Cabin
Historic Hanover Area Home, 16 Miles to Dartmouth!
Exterior

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!
Cozy Crescent Cottage
Pink sky sunsets

Cozy Crescent Cottage

10.0 out of 10, Exceptional, (24)
"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
Charming Cavendish Cottage: All-Season Retreat!
Cavendish Vacation Rental | 3BR | 3BA | 1,500 Sq Ft | Stairs Required

Charming Cavendish Cottage: All-Season Retreat!

2.0 star property
10.0 out of 10, Exceptional, (4)
"Such a wonderful and warm home. Other than condiments the kitchen was well stocked with dishes, cups and small appliances. The back screened in porch was a peaceful retreat for morning coffee and devotions and a great place to wind down at night. The owner was very nice and accommodating. The minute we walked in we were in awe of Rosehill Cottage. We will definitely stay here again if we are in the area."
Charming Cavendish Cottage: All-Season Retreat!
Newbury Family Getaway: Walk to Lake Sunapee
Newbury Vacation Rental | 3BR | 1BA | 1,200 Sq Ft | Stairs Required

Newbury Family Getaway: Walk to Lake Sunapee

2.0 star property
Newbury Family Getaway: Walk to Lake Sunapee
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly

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

9.2 out of 10, Wonderful, (15)
"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
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

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

9.6 out of 10, Exceptional, (9)
"This lake house is absolutely everything you would expect from a five star rated home. It is a newly renovated lake front home. The house is located about 3 miles north of Ludlow. The property was clean and well maintained. We visited on Columbus Day weekend for our daughter’s wedding. We will return some day in the summer to enjoy the lake. I would recommend this property to my family and friends. Thank you for sharing your home with us during this special time for our family. "
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit
Cozy Historic Hilltop Cottage with Mount Ascutney View
Cottage on the hill

Cozy Historic Hilltop Cottage with Mount Ascutney View

9.6 out of 10, Exceptional, (75)
"This house is exactly as described. It is in a very attractive location with good views and is very private. The house is much larger inside than it appears from the photos but still very cozy and is well equipped. It was spotlessly clean."
Cozy Historic Hilltop Cottage with Mount Ascutney View
The Cairn, 1840s Cozy Stone Cottage, Pet Friendly
Exterior

The Cairn, 1840s Cozy Stone Cottage, Pet Friendly

10.0 out of 10, Exceptional, (7)
"Everything was wonderful from the very beginning… The ease of booking, payment, check-in, property, check out, it was all perfect! The house was in a great neighborhood, very quaint, and just the perfect size for the six of us. Well maintained and clean, had everything we could possibly need. Highly recommend."
The Cairn, 1840s Cozy Stone Cottage, Pet Friendly
Spruce Moose Cottage | Tiny House on 65 private acres

Spruce Moose Cottage | Tiny House on 65 private acres

Spruce Moose Cottage | Tiny House on 65 private acres
Cozy cottage on the river, minutes from skiing, horse events, and so much more!
Living area

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!
Charming Lakefront Cottage near Mount Sunapee
Large side patio with outdoor dining, charcoal grill, and lots of comfy seating.

Charming Lakefront Cottage near Mount Sunapee

10.0 out of 10, Exceptional, (35)
"Great girls weekend getaway celebrating a friends 50th! Clean, cozy and a GORGEOUS fall weather weekend made it even more amazing, from the waterfront to the foliage reflecting off the water like glass, to the fire pit! Absolute perfection! Thank you for sharing your beautiful home! ~ Amy"
Charming Lakefront Cottage near Mount Sunapee
Lakeside life at its best!
Looking back from shoreline at dusk.

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!
4bdrm Cottage central to year round fun w/fireplace
Exterior

4bdrm Cottage central to year round fun w/fireplace

4bdrm Cottage central to year round fun w/fireplace
Private Sunapee Getaway: 2 Mi to Ledge Pond!
Exterior

Private Sunapee Getaway: 2 Mi to Ledge Pond!

3.0 star property
Private Sunapee Getaway: 2 Mi to Ledge Pond!
Weston Vacation Rental - Close to Ski Resorts!
Living area

Weston Vacation Rental - Close to Ski Resorts!

3.0 star property
Weston Vacation Rental - Close to Ski Resorts!
Historic New Hampshire Home: 1 Mi to Boat Launch
Property grounds

Historic New Hampshire Home: 1 Mi to Boat Launch

3.0 star property
Historic New Hampshire Home: 1 Mi to Boat Launch
Luxury Vermont Vacation Rental: Private Hot Tub!
Dining

Luxury Vermont Vacation Rental: Private Hot Tub!

3.0 star property
Luxury Vermont Vacation Rental: Private Hot Tub!
Wooded Waterfront Grantham Home < 10 Mi to Ski!
Terrace/patio

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!
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
Front of property

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (40)
"Like property— sad the lift that made it ski and in out was closed due weather conditions "
The price is SAR 1,983
SAR 2,678 total
includes taxes & fees
10 Jan - 11 January 2025
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Beautiful Myrtle Beach Condo with Amenities Galore

Beautiful Myrtle Beach Condo with Amenities Galore

8.8 out of 10, Excellent, (161)
"This was a really nice spacious property. It was very clean and in a nice location. "
Beautiful Myrtle Beach Condo with Amenities Galore
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
Located in the Okemo Mt. Community, a mile to the base lodge

Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

9.8 out of 10, Exceptional, (164)
"The property is exactly like the pictures indicate. The house is in a friendly neighborhood outside of town. The house is very comfortable and spacious. The host responds to your messages in timely manner, and, she is very workable. Would definitely stay there again "
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
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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