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Search Windsor Cottage Rentals from CA $245

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Browse Select Windsor Cottages

Addie's Place: A Quiet and Quirky Private Guesthouse
Relax in a serene room with a wicker chair and a view of the lush garden.

Addie's Place: A Quiet and Quirky Private Guesthouse

10.0 out of 10, Exceptional, (1)
"I used to call this quiet neighborhood home, and it was a treat to be back briefly. The space is quiet but charming, with a nicely appointed bathroom and a comfortable bed. Love the colorful decor. "
The price is CA $245
CA $395 total
includes taxes & fees
Sep 4 - Sep 5
Addie's Place: A Quiet and Quirky Private Guesthouse
Woodstock Village Carriage House
Set amidst lush greenery, this traditional building offers a serene and retreat with a gabled roof and symmetrical facade.

Woodstock Village Carriage House

9.6 out of 10, Exceptional, (92)
"Location was great!!"
Woodstock Village Carriage House
The Cairn, 1840s Cozy Stone Cottage, Pet Friendly
Relax in the cottage's outdoor seating area, featuring a wicker chair, cushioned bench, and small table.

The Cairn, 1840s Cozy Stone Cottage, Pet Friendly

10.0 out of 10, Exceptional, (13)
"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
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit
Escape to a secluded cabin surrounded by tall trees, featuring a cozy porch and outdoor speakers for a peaceful retreat.

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

9.8 out of 10, Exceptional, (16)
"We loved the house and especially the location. The views are beautiful and the proximity to town, the mountain and parks make it a fantastic spot to stay."
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit
Cozy cottage on the river, minutes from skiing, horse events, and so much more!
Enjoy cooking in this well-equipped kitchen with a stainless steel sink, toaster, microwave, and stove with digital controls.

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

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

10.0 out of 10, Exceptional, (2)
"What a charming stay in a vintage cottage, lovingly updated. The views of the lake are spectacular and accessible. Lots to do from this starting point but I decided to kick back and relax - a perfect spot!"
Sweet vintage cottage on Mountain View Lake, 2024 updates, next to Lake Sunapee
Historic Hanover Area Home, 16 Miles to Dartmouth!
House (4 Bedrooms) | Interior

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!
Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!
Enjoy cooking in this kitchen with a window view of lush greenery.

Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!

3.0 star property
Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!
Cozy Historic Hilltop Cottage with Mount Ascutney View
Set amidst a serene wooded area, this charming home features a traditional gabled roof and a central chimney.

Cozy Historic Hilltop Cottage with Mount Ascutney View

9.6 out of 10, Exceptional, (78)
"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
Historic New Hampshire Home: 1 Mi to Boat Launch
House (3 Bedrooms) | Interior

Historic New Hampshire Home: 1 Mi to Boat Launch

3.0 star property
Historic New Hampshire Home: 1 Mi to Boat Launch
Lakeside life at its best!
Escape to a secluded cabin surrounded by lush forest and a tranquil atmosphere.

Lakeside life at its best!

9.8 out of 10, Exceptional, (47)
"This tucked-away house is beautifully designed and maintained, and is very comfortable. The views of the lake are wonderful. A great get-away! The owners are friendly, responsive, and accommodating."
Lakeside life at its best!
Picture-perfect Vermont Mtn Cabin w/ Hot Tub!
House (6 Bedrooms) | Interior

Picture-perfect Vermont Mtn Cabin w/ Hot Tub!

3.0 star property
Picture-perfect Vermont Mtn Cabin w/ Hot Tub!
Wooded Waterfront Grantham Home < 10 Mi to Ski!
Relax in this inviting living area with a high ceiling, two sofas, and a cozy ottoman.

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!
Lovely Ludlow Farmhouse ~ 1 Mi to Town & Slopes!
House (3 Bedrooms) | Interior

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!
Relax on the deck with a hammock and comfortable seating.

Pet-friendly Claremont Vacation Rental!

3.0 star property
Pet-friendly Claremont Vacation Rental!
Luxury Vermont Vacation Rental: Private Hot Tub!
House (4 Bedrooms) | Interior

Luxury Vermont Vacation Rental: Private Hot Tub!

3.0 star property
Luxury Vermont Vacation Rental: Private Hot Tub!
Inviting Vermont Home On Mount Ascutney!
Relax in a serene bedroom with a large bed, bedside table, and potted plant.

Inviting Vermont Home On Mount Ascutney!

3.0 star property
Inviting Vermont Home On Mount Ascutney!
Private Sunapee Getaway: 2 Mi to Ledge Pond!
Cozy cabin interior with a dining area, seating area, and fireplace.

Private Sunapee Getaway: 2 Mi to Ledge Pond!

3.0 star property
Private Sunapee Getaway: 2 Mi to Ledge Pond!
18 Mi to Skiing: Colorful Home in Springfield!
House (3 Bedrooms) | Interior

18 Mi to Skiing: Colorful Home in Springfield!

3.0 star property
18 Mi to Skiing: Colorful Home in Springfield!
Ski-Hike-Relax! Remodeled cottage with White River access in the Green Mountains
Relax on the front porch with two chairs and a small table, surrounded by lush greenery.

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
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 Hotel Reviews

Hilton Garden Inn Hanover Lebanon

Hilton Garden Inn Hanover Lebanon

10/10 Excellent
"Great place"
Tim 1-night trip
Posted 2 days ago
Hilton Garden Inn Hanover Lebanon