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Chesapeake Bay Winter Rentals & Holiday Homes

Discover winter rentals Chesapeake Bay - We found 10069 exact matches

About Chesapeake Bay Winter Rental on Rent By Owner

Planning on a winter vacation in Chesapeake Bay? Discover 10069 places to stay in Chesapeake Bay, for those traveling with their family, friends, in groups, or for a wedding retreat.

At Rent By Owner, we have a wide range of listings for accommodations in Chesapeake Bay, MD that are perfect for your winter trip or seasonal escape. Our listings have private vacation homes, cabins, condos, villas, resorts, or pet-friendly apartments that you would love. RBO winter vacation homes have top amenities, including Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.

Chesapeake Bay winter accommodation starts at US $382, and the most popular properties in Chesapeake Bay are cabins, bungalows, and rental homes by owner. Planning snowboarding on your next winter vacation? We have many snowboard-friendly ski resorts, chalets, and cabins that are available for you to rent. These rentals are available for both short-term stays and long-term stays, whether you are traveling for a weekend, monthly, or a longer stay, RBO will make your winter trip memorable.

Rent By Owner offers a great deal for travelers planning on renting a place in Chesapeake Bay, to enjoy these benefits and to book your winter vacation homes, go to RBO filter option, enter your travel date, check the filters to narrow down your property type and amenities, then choose from a long list of our winter vacation rentals without hassle. Our interactive map is also available, to view all places to stay in or around Chesapeake Bay and unlock even more amazing deals.

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Frequently Asked Questions About Chesapeake Bay Winter 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 Winter Rentals in Chesapeake Bay:

The average cost for winter rentals in Chesapeake Bay is $382 per night. RBO has a wide list of great winter places to stay near Chesapeake Bay that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Yes, here are the top cottage/chalet rentals in Chesapeake Bay that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Chesapeake Bay on Rent By Owner

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Chesapeake Bay to find what works for you.
As of 2025, the data from Rent By Owner shows that there are over 10069 private swimming pools or indoor pools accommodations near Chesapeake Bay along with other great amenities.