Photo by William E Berry Jr.

Search Cottages in Windsor

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
20 Jun - 22 Jun
In two weeks
27 Jun - 29 Jun
In one month
11 Jul - 13 Jul
In two months
8 Aug - 10 Aug

Cottages in Windsor

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

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
The Cairn, 1840s Cozy Stone Cottage, Pet Friendly
Exterior

The Cairn, 1840s Cozy Stone Cottage, Pet Friendly

10.0 out of 10, Exceptional, (11)
"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
Cozy Crescent Cottage
Terrace/patio

Cozy Crescent Cottage

10.0 out of 10, Exceptional, (27)
"Cozy, full of character and calming. We look forward to returning."
Cozy Crescent Cottage
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit
Interior

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

9.8 out of 10, Exceptional, (12)
"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
Woodstock Village Carriage House
Exterior

Woodstock Village Carriage House

9.6 out of 10, Exceptional, (91)
"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
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly
Fridge, microwave, oven, stovetop

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

9.2 out of 10, Wonderful, (17)
"We thoroughly enjoyed our stay at the cottage. We slept well and the location was perfect. We would like to visit again!"
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly
Brook Road Cabin
Exterior

Brook Road Cabin

3.5 star property
7.8 out of 10, Good, (9)
"In the aftermath of 30+ā€ 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. šŸ˜Š"
Brook Road Cabin
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!
Addie's Place: A Quiet and Quirky Private Guesthouse
Exterior

Addie's Place: A Quiet and Quirky Private Guesthouse

The price is AEDĀ 580
AEDĀ 988 total
includes taxes & fees
15 Jul - 16 Jul
Addie's Place: A Quiet and Quirky Private Guesthouse
Cozy Historic Hilltop Cottage with Mount Ascutney View
Exterior

Cozy Historic Hilltop Cottage with Mount Ascutney View

9.8 out of 10, Exceptional, (76)
"Great location for our vacation. Owner was bery quick to respond to questionsz"
Cozy Historic Hilltop Cottage with Mount Ascutney View
Pet-friendly Claremont Vacation Rental!
House (5 Bedrooms) | Interior

Pet-friendly Claremont Vacation Rental!

3.0 star property
Pet-friendly Claremont Vacation Rental!
Cozy cottage on the river, minutes from skiing, horse events, and so much more!
Fridge, microwave, oven, stovetop

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!
Lovely Ludlow Farmhouse ~ 1 Mi to Town & Slopes!
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!
Lakeside life at its best!
Exterior

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. Itā€™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!
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, (9)
"If youā€™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
Picture-perfect Vermont Mtn Cabin w/ Hot Tub!
House (6 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Picture-perfect Vermont Mtn Cabin w/ Hot Tub!

3.0 star property
Picture-perfect Vermont Mtn Cabin w/ Hot Tub!
Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!
Interior

Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!

3.0 star property
Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!
18 Mi to Skiing: Colorful Home in Springfield!
Interior

18 Mi to Skiing: Colorful Home in Springfield!

3.0 star property
18 Mi to Skiing: Colorful Home in Springfield!
Inviting Vermont Home On Mount Ascutney!
Microwave, oven, stovetop, dishwasher

Inviting Vermont Home On Mount Ascutney!

3.0 star property
Inviting Vermont Home On Mount Ascutney!
Chester Farmhouse on 100 Acres, 15 Min to Okemo!
Interior

Chester Farmhouse on 100 Acres, 15 Min to Okemo!

3.0 star property
Chester Farmhouse on 100 Acres, 15 Min to Okemo!
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Frequently asked questions

Why book your cottage in Windsor with Expedia?
Expedia has some terrific cottages in Windsor, so start packing your bags for an unforgettable stay on natureā€™s doorstep. If you need to stick to a budget, choose how much youā€™d like to spend and the preferred star rating of your property. Or, try out our filters to search for cottages with a hot tub or free WiFi. Weā€™ll help you find the right place whatever your bank balance or plans.
How can I find cheap cottages in Windsor?
With Expediaā€™s filter tool, comparing cheap cottages in Windsor couldnā€™t be easier. To discover stays thatā€™ll make your wallet smile, narrow your search by budget, amenities and star rating.