Windsor County Cottage Rentals & Holiday Homes
Find the best cottages in Windsor County - We found 190 exact matches
About Windsor County Luxury Rental on Cottage Romance
Searching for cottages to rent near Windsor County? Cottage Romance features more than 190 cottages that are perfect for your next trip. Discover luxury cottage rentals that are a few miles away from the lake or beach. These cottage rentals in Windsor County have hot baths, are kid-friendly & family-friendly, and are near top local attraction spots, to give guests the best travel experience they could ever wish for. Cottage Romance’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Windsor County.
Are you planning to travel to the lakeside, beach, or mountain area? Cottage Romance’s cottage rentals offers a wide selection, giving you direct access to the owners of these cottage rentals, and offering you the best opportunity to find a good price.
Cottage Romance boasts of 190 holiday cottages and places to stay in Windsor County. The site provides unique Airbnb, VRBO, Cottage Romance-style cottages to fit your trip or get away with your friends and family. This can be a weekend getaway, spring break, summer vacation, or annual holiday -- all fitting within your budget.
Frequently Asked Questions About Windsor County Cottage Rentals
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:
- Sunset Cabin - your private romantic hideaway
- Cabin in the Orchard near Silver Lake
- Beautiful Log Cabin in Weston, VT
- Vermont Cottage Amherst Lake & Sanctuary~Route100~Pets~Okemo & Killington
- Little Cabin On The Ridge Andover Vt
- Secluded and Serene - GET AWAY FROM IT ALL! Barnard, VT
- Mountainview Lodge - Newly Renovated Luxury Home <1 Mile To Okemo!
- Log Cabin Retreat on 40 Acres
- Vacation Rental - Choose from 5 nearby mountains or relax in peace & comfort
- Cozy Ski-House by Okemo Hot Tub & Mountain Privacy
How much does it cost to rent a cottage in Windsor County?
The average cost for a cottage rental in Windsor County is $424 per night. Cottageromance 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:
- 11 BR, 7 Bth, 1/2 mile to Okemo, Hot Tub, on Ski Shuttle, King Bed, Walk to Town
- Picture-Perfect Vermont Mtn Cabin with Hot Tub!
- Bear Hill Cabin 4 Bedroom Cabin
- Log Cabin home with Mt Ascutney views and pool table
See all pet-friendly vacation rentals in Windsor County on Cottageromance
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 Cottageromance shows that there are Over 190 private swimming pools or cottages with indoor pools in the Windsor County area along with other great amenities.
