Old Windsor Cottage Rentals & Holiday Homes

Find the best cottages in Old Windsor - We found 54 exact matches

About Old Windsor Cottage Rentals on PickleTrip

Searching for cottages to rent near Old Windsor? PickleTrip™ features more than 54 cottages that are perfect for your next pickleball getaway. Plan your ultimate holiday and discover luxury cottage rentals that are a few miles away from the lake or beach and have access to private courts or nearby facilities. These cottage rentals in Old 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. PickleTrip™’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Old Windsor.

Are you planning to travel to the lakeside, beach, or mountain area? PickleTrip™’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.

PickleTrip™ boasts of 54 holiday cottages and places to stay in Old Windsor. The site provides unique Airbnb, VRBO, pickleball-ready 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.

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Frequently Asked Questions About Old Windsor Rental Cottages

There are a lot of options in Old Windsor. If you plan on staying in the Old 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 Old Windsor:

The average cost for a cottage rental in Old Windsor is $388 per night. PickleTrip has a wide list of great cottages near Old Windsor that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Yes, here are the top cottage rentals in Old Windsor that allow you to bring your pet:

See all pet-friendly vacation rentals in Old Windsor on PickleTrip

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Old Windsor to find one that works for you.
As of 2025, the data from PickleTrip shows that there are Over 54 private swimming pools or cottages with indoor pools in the Old Windsor area along with other great amenities.
About 54 cottages in Old Windsor boast of premium hot tubs. Some of the popular places to stay with hot tubs include:See all holiday vacation rentals in Old Windsor on PickleTrip
Yes, there are luxury cottages in Old Windsor. Find more luxury, lakefront, winter, & last-minute cottage rentals near Old Windsor.