What are the top rated Cottage Rentals in Windsor County?

There are a lot of options in Windsor County. If you plan on staying in the Windsor County 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 County: <a href="/property/alpine-farm-cottage-retreat/HA-3212150900" class="class="static-page-link"">Alpine Farm Cottage Retreat</a> <a href="/property/ski-hike-relax-remodeled-cottage-with-white-river-access-in-the-green-mountains/HA-3213194512" class="class="static-page-link"">Ski-Hike-Relax! Remodeled cottage with White River access in the Green Mountains</a> <a href="/property/ronnoco-farm-charming-brownsville-west-windsor-vt-cottage/HA-3212304415" class="class="static-page-link"">Ronnoco Farm-Charming Brownsville/West Windsor, VT cottage</a> <a href="/property/charming-3-bedroom-cottage-in-enchanting-south-woodstock-steps-to-gmha/HA-3214133973" class="class="static-page-link"">Charming 3-bedroom cottage in enchanting South Woodstock. Steps to GMHA!</a> <a href="/property/charming-4-bedroom-cottage-in-weston-vermont-close-to-ski-resorts/HA-3214180360" class="class="static-page-link"">CHARMING 4-bedroom cottage in Weston, Vermont. CLOSE TO SKI RESORTS</a> <a href="/property/new-listing-rustic-charm-meets-modern-comfort-at-rock-haven-sugar-house-in-reading-vt/HA-3214097383" class="class="static-page-link"">NEW LISTING Rustic Charm Meets Modern Comfort at Rock Haven Sugar House in Reading, VT</a> <a href="/property/new-lakeside-cottage-near-okemo-and-killington/HA-1214091397" class="class="static-page-link"">New Lakeside Cottage near Okemo and Killington</a> <a href="/property/charming-cavendish-cottage-all-season-retreat/HA-1219969527" class="class="static-page-link"">Charming Cavendish Cottage: All-Season Retreat!</a> <a href="/property/cozy-1850s-home-on-the-riverfront-with-mountain-river-views-dog-friendly/HA-3213025968" class="class="static-page-link"">Cozy 1850s home on the riverfront with mountain &amp; river views - dog-friendly</a> <a href="/property/cottage-across-street-from-the-lake-w-60-water-frontage-access-private-dock/HA-321982270" class="class="static-page-link"">Cottage Across Street from the Lake w/60&#39; Water Frontage Access, Private Dock</a>

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

The average cost for a cottage rental in Windsor County is $409 per night. Cartagenacaribbeantours has a wide list of great cottages near Windsor County that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in Windsor County that allow pets?

Yes, here are the top cottage rentals in Windsor County that allow you to bring your pet: Cozy cottage on the river, minutes from skiing, horse events, and so much more! Green Door Cottage Ludlow Ski Cabin 2 Mi to Ski Parking Peaceful Riverview Retreat - 1 mi to Dartmouth College - 4-bd -3ba <a href="/all/usa/vermont/windsor-county" class="class="static-page-link"">See all pet-friendly vacation rentals in Windsor County on Cartagenacaribbeantours</a>

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

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

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

As of 2026, the data from Cartagenacaribbeantours shows that there are Over 44 private swimming pools or cottages with indoor pools in the Windsor County area along with other great amenities.

Windsor County Cottage Rentals By Owner

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

From US $206

10.0 (13 Reviews)

Cottage

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

Air Conditioner
Parking
TV

Windsor County Cottage Rentals & Holiday Homes

Find the best cottages in Windsor County - We found 44 exact matches

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