What are the top rated Cottage Rentals in Windsor?

There are a lot of options in Windsor. If you plan on staying in the Windsor area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Windsor: <a href="/property/meadow-view-35-acres-outside-your-door/HA-1217195192" class="class="static-page-link"">Meadow View- 35 Acres outside your door</a> <a href="/property/sunset-cabin-your-private-romantic-hideaway/HA-1214638923" class="class="static-page-link"">Sunset Cabin - your private romantic hideaway</a> <a href="/property/beautiful-home-offering-privacy-on-7-acres-with-private-pond/HA-3212193520" class="class="static-page-link"">Beautiful home offering privacy on 7 acres with private pond</a> <a href="/property/snapdragon-inn/BC-381142" class="class="static-page-link"">Snapdragon Inn</a> <a href="/property/antique-farmhouse-with-spectacular-mountain-view-in-a-bucolic-setting/HA-3214358955" class="class="static-page-link"">Antique farmhouse with spectacular mountain view in a bucolic setting.</a> <a href="/property/luxury-vermont-vacation-rental-private-hot-tub/BC-10164847" class="class="static-page-link"">Luxury Vermont Vacation Rental Private Hot Tub!</a> <a href="/property/exquisite-log-home-with-views-near-woodstock-vermont/HA-121124894" class="class="static-page-link"">Exquisite Log Home with views near Woodstock, Vermont</a> <a href="/property/long-range-mountain-views-in-west-windsor/HA-3212015712" class="class="static-page-link"">Long Range Mountain Views in West Windsor</a> <a href="/property/lovely-vermont-cabin-on-a-quiet-street/HA-3213210284" class="class="static-page-link"">Lovely Vermont Cabin on a quiet street</a> <a href="/property/luxury-vermont-vacation-rental-private-hot-tub/HA-1219833561" class="class="static-page-link"">Luxury Vermont Vacation Rental: Private Hot Tub!</a>

How much does it cost to rent a cottage in Windsor?

The average cost for a cottage rental in Windsor is $210 per night. Villa Bay has a wide list of great cottages near Windsor that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in Windsor that allow pets?

Yes, here are the top cottage rentals in Windsor that allow you to bring your pet: Cozy Historic Hilltop Cottage with Mount Ascutney View Beautiful home offering privacy on 7 acres with private pond Luxury Vermont Vacation Rental Private Hot Tub! Antique farmhouse with spectacular mountain view in a bucolic setting. Snapdragon Inn <a href="/all/usa/vermont/windsor" class="class="static-page-link"">See all pet-friendly vacation rentals in Windsor on Villa Bay</a>

Do you have any rental cottages in Windsor that are suitable for families?

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Windsor to find one that works for you.

Are there quality cottages in Windsor that have indoor swimming pools?

As of 2026, the data from Villa Bay shows that there are Over 1 private swimming pools or cottages with indoor pools in the Windsor area along with other great amenities.

Windsor Cottage Rentals By Owner

Cozy Historic Hilltop Cottage with Mount Ascutney View

From US $210

9.6 (84 Reviews)

Cottage

Cozy Historic Hilltop Cottage with Mount Ascutney View

Parking
Pool
TV

Windsor Cottage Rentals & Holiday Homes

Find the best cottages in Windsor - We found 1 exact matches

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