Search Chesapeake Bay Cottage Rentals from CA $281

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Browse Select Chesapeake Bay Cottages

Situated on a wooden dock, this house offers serene waterfront views from its balcony.

"Beautiful pool areas, lots to do, and plenty of room with a family of 5! "

CA $316 total

includes taxes & fees

Sep 8 - Sep 9

Set against a serene backdrop, this house features a beautifully lit facade and a decorative reindeer sculpture on the lawn.

"We stay at Firefly every time we go to visit our son and his family. It works perfectly for us…an oasis for us, and a fun place for the kids to visit, too. Pat and Ken have been the perfect hosts!"

Traditional home with a gabled roof and central chimney, set amidst a peaceful grassy lawn and trees.

"This was a cute historic house very close to all shops and restaurants. Location could not be better. It could use a thorough cleaning and the shower is pretty rustic. But overall a good place to stay."

Relax on the beach with lounge chairs and a shaded gazebo overlooking the calm waters.

"Lovely , peaceful mini vacation"

"The location is great for a family with pets. The check in and out process was simple and the host was responsive. No complaints! "

Relax on the deck or patio, surrounded by a beautifully maintained garden and a wooden fence.

"It was beautiful clean and very nice people"

Traditional two-story home with a central chimney and wrap-around porch, set amidst well-mainters landscaping.

"This listing says cottage but it's an apartment. Be ready to go up stairs to get into it. The kitchen is small but fine. Everything works, but it's not especially well equipped for cooking. The coffee maker does not work. Our checkin was delayed for about 40 minutes when we arrived and we had no where to stay while waiting for our apartment. Wi Fi was very weak in the apartment and TV is like a hotel where there are certain channels available but no way to sign in to your own streaming accounts....

Traditional house with a front porch surrounded by lush gardens and flowering plants.

"Easy checkin/checkout. Cute cottage. Scenic and comfortable."

Walk along the boardwalk to the wide, open beach.

"Our stay was nice. The house was clean."

Cozy home with a front porch and well-manicured yard.

"My three sisters and I had a wonderful stay! The house was clean, updated, and in a great location. We highly recommend!"

Guest house with a covered porch, surrounded by a white picket fence and landscaped grounds.

"Wonderful golf cart community! Perfect way to relax, short walk to the water in either direction. Meet allot of the locals, enjoyed the local breweries and restuarants."

A charming single-story building with a white door and decorative iron grilles adorns the facade.

"older place but very nice and close to the beach"

"It was alright "

Situated in a residential area, this cabin offers a peaceful retreat surrounded by mature trees and a grassy yard with ocean views.

"Great place, cozy and easy to park and get around. "

Enjoy a serene beach experience with access to the ocean.

"If you’re looking for a place for you to have a safe space with your family, young or old, with all the amenities that you would want from your own home this is it. If you’re a veteran, there’s multitude of bases nearby with commissary’s to get groceries for the week to help the budget. "

Enjoy a peaceful outdoor space with a table, chairs, and umbrella, surrounded by a tree and scenic views.

"Perfect house for a long weekend. Clean, cozy and great communication with Maxine. Would definitely stay here again when I return to Cambridge. "

Explore a charming multi-level structure surrounded by lush trees, featuring a balcony with a railing and windows with curtains.

"Repeat guest.. stayed in another unit previously *loft property.Property is very close to the beach, can walk into the sand from the property. Pet friendly is a plus.. lots of doggos on the beach.Property has the basics.. minimal items in unit, so you need to bring quite a bit of things to make your trip complete. Owners have several units, so amenities are shared. Husband and I used the charcoal grill and set by the firepit in the sand. Not sure id stay in this particular unit again, but id...

Enjoy a patio surrounded by lush trees and a well-manicured lawn.

"Great spot for a weekend visit. Second time staying. Great communication with owner. Will stay again"

Enjoy a home away from home with a front porch and a deck area.

"The Salty Sailor was an excellent, affordable, and pet friendly rental. Nice location on ridge rd next to Mr Baldys which is a must to try if you stay here. The rooms are a bit older but maintained well. I didn’t experience any of the conditions that were listed in the other reviews here. We would certainly stay here again."