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Chesapeake Bay, United States of America

Chesapeake Bay vacation rentals

We found 9,351 vacation rentals — enter your dates for availability

Discover a selection of 9,000 vacation rentals in Chesapeake Bay, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $125 per night, and houses and cabins are popular options for a stay in Chesapeake Bay. Either way, you'll find a rental for everyone's needs.
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Find the best place to stay — Chesapeake Bay

Family friendly home near Colonial Williamsburg and Busch Gardens

3 Bedrooms · 2 Bathrooms
$150 avg/night
(1)

Washington DC Suburb with Quite Neighborhood Just A Stones Throw From Everything

Sleeps 12 · 5 Bedrooms · 3 Bathrooms
$125 avg/night
(117)

Newly Renovated Dwntwn 3 BR House W PrivateParking

3 Bedrooms · 1 Bathroom
$207 avg/night

Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

Sleeps 5 · 2 Bedrooms · 2 Bathrooms
$184 avg/night
(132)

Search 9,351 vacation rentals

Top rated rentals — Chesapeake Bay
Stayed Jan 2023

Couldn't ask for more

Had a joyful two nights with my wife of 41 years. The host went to great lengths to make their home as welcoming as possible. The house was adorned with homemade crafts which gave the place even more personality. The screened in porch and view of the...

Gene P.
Gene P.

Richmond

Stayed Jan 2023

Fantastic Girl's Weekend

This houseboat was STUNNING. Beautiful, fun property that is close to food, attractions and shopping. It was the perfect place to get away with friends. We loved the spaces, attention to detail, and thoughtfulness of the hosts. I wish I could upload ...

Lori K.
Lori K.
Stayed Jan 2023

well-maintained property in a peaceful neighborhood

We quite enjoyed our little winter trip to Chincoteague and this house provided the perfect place to relax. It is close to everything, including the wildlife refuge (we visited every day), but is tucked away in a quiet neighborhood with nice water vi...

Kirstin M.
Kirstin M.
Stayed Jan 2023

Peaceful Stay On the Cliff

We had a great time at the Navy Cabin. Brett was very attentive and made sure we arrived smoothly and knew the ins and outs of the cabin. The view was incredible and the surrounding area was quaint and quiet. We went for a walk at the nearby American...

Nick G.
Nick G.
Stayed Jan 2023

Perfect for two

Everything about this location is great for two. It’s small but very cozy and clean. Jack is a top tier property manager and even though we had to cut out early, let me bank my unused nights for a future visit. We were on a work trip with 4 of us, wi...

frank d.
frank d.
Stayed Dec 2022

Cape Charles New Year

Quick getaway for the holiday weekend. Excellent communication and follow-up. Very clean and well appointed home. Great location. Cape Charles drops a “Crab Pot” for the new year celebration. The next morning is a fun polar bear plunge into the bay..

Kathleen S.
Kathleen S.
Stayed Dec 2022

Wonderful House and Location

We stayed the week between Christmas and New Years so we obviously weren't planning on enjoying the outdoor amenities. :) The view was exactly what we wanted though. Even the back of the house had views of some water off in the distance. Everything w...

MIchelle H.
MIchelle H.
Stayed Dec 2022

Yorktown Jamestown Williamsburg Gloucester Point

Truly a comfortable stay on the island with a total of 3 homes! Google thinks this home is off to the right so don't be fooled in the dark she is the first cottage over the wood Bridge turn in thr driveway on the left! Once you are there RELAX and ta...

Cindy G.
Cindy G.
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How many vacation rentals are available around Chesapeake Bay, US?

Our 2023 property listings offer a large selection of 9,351 vacation rentals around Chesapeake Bay. From 4,798 house rentals to 448 cabin rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

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