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Chesapeake Bay Cottage Rentals & Holiday Homes

Find the best cottages in Chesapeake Bay - We found 726 exact matches

About Chesapeake Bay Cottage Rentals on PickleTrip

Searching for cottages to rent near Chesapeake Bay? PickleTrip™ features more than 726 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 Chesapeake Bay 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 Chesapeake Bay.

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 726 holiday cottages and places to stay in Chesapeake Bay. 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 Chesapeake Bay Rental Cottages

There are a lot of options in Chesapeake Bay. If you plan on staying in the Chesapeake Bay area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Chesapeake Bay:

The average cost for a cottage rental in Chesapeake Bay is $321 per night. PickleTrip has a wide list of great cottages near Chesapeake Bay 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 Chesapeake Bay that allow you to bring your pet:

See all pet-friendly vacation rentals in Chesapeake Bay on PickleTrip

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Chesapeake Bay to find one that works for you.
As of 2026, the data from PickleTrip shows that there are Over 726 private swimming pools or cottages with indoor pools in the Chesapeake Bay area along with other great amenities.
About 726 cottages in Chesapeake Bay boast of premium hot tubs. Some of the popular places to stay with hot tubs include:See all holiday vacation rentals in Chesapeake Bay on PickleTrip
Yes, there are luxury cottages in Chesapeake Bay. Find more luxury, lakefront, winter, & last-minute cottage rentals near Chesapeake Bay.