Windsor Cottage Rentals & Holiday Homes
Find the best cottages in Windsor - We found 68 exact matches
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About Windsor Cottage Rentals on Nantucket Beach Cottage
Searching for cottages to rent near Windsor? Nantucket Beach Cottage features more than 68 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 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. Nantucket Beach Cottage’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Windsor.
Are you planning to travel to the lakeside, beach, or mountain area? Nantucket Beach Cottage’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.
Nantucket Beach Cottage boasts of 68 holiday cottages and places to stay in Windsor. The site provides unique Airbnb, VRBO, Nantucket Beach Cottage-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 Cottage Rentals
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:
- Country Living in Mattoon
- Quaint and colorful with fun amenities!
- The Lake Loft: Minutes from Lake Shelbyville & Above Game On
- Large Home w/game room, grill, and hot tub
- The Firefly Lodge on Lake Shelbyville - Fully Updated Cabin with Lake Access
- Beautiful vacation home seconds away from Lake Shelbyville Beach and Boat Ramp!
- Stunning Property with loads of amenities. In ground pool, pet friendly, with photo opps galore!
- Newly updated and cozy home! Located near downtown!
- Gateway Inn
- The Shelby Inn
How much does it cost to rent a cottage in Windsor?
The average cost for a cottage rental in Windsor is $251 per night. Nantucketbeachcottage 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:
- Paradise Found in Illinois
- A Novel Stay 3 bed 2 bath log cabin in Shelbyville, IL
- The Shelby Inn
- Binion Lodge: Wooded Privacy Near Lake Shelbyville
See all pet-friendly vacation rentals in Windsor on Nantucketbeachcottage
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 Nantucketbeachcottage shows that there are Over 68 private swimming pools or cottages with indoor pools in the Windsor area along with other great amenities.