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Chesapeake Bay Summer Rentals, Cottages & Cabins

Book a Place to Stay in Chesapeake Bay for Your Summer Getaway

About Chesapeake Bay Summer Rental on Rent By Owner

With 15731 summer rentals in or near Chesapeake Bay, choosing a suitable rental home for your upcoming summer getaway on Rent By Owner is easy. Whether you are traveling with family, friends, or in a group to Chesapeake Bay or areas nearby, RBO has plenty of summer accommodations to choose from, many with top amenities such as private pools, indoor/outdoor pools, hot tubs, WiFi, beach access, nearby parks, luxury bedrooms, bathtubs, and pet-allowed environments.

Looking for a relaxing place to stay in Chesapeake Bay for a summer vacation you do not want to forget easily? Rent By Owner summer rental homes are available to provide you with the maximum comfort you deserve. Whether you're needing a unique style condo, luxury resort, villas, bungalow, cozy cabin, RV, or cottage in Chesapeake Bay, RBO has got you covered for your next summer holiday.

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Frequently Asked Questions About Chesapeake Bay Luxury Rentals

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 Summer Rentals in Chesapeake Bay:

In 2025, RBO offers 15731 summer rentals in or around Chesapeake Bay. Find unique home rentals for your summer holiday or a weekend getaway with family and friends.
The average price per night for a summer rental in Chesapeake Bay is $349. Check the full list of summer accommodations in Chesapeake Bay.
There are 15731 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with Rent By Owner.

Yes, here are some popular summer holiday rentals in Chesapeake Bay that have a private or indoor pool:

Check all holiday rentals with a pool in Chesapeake Bay on Rent By Owner.