Search Chesapeake Bay Cottage Rentals from CA $299

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Browse Select Chesapeake Bay Cottages

Our top choices for Chesapeake Bay cottages

"Great place to stay!"

CA $336 total

includes taxes & fees

Sep 1 - Sep 2

"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!"

"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."

"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! "

"It was beautiful clean and very nice people"

"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....

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

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

"Very clean, exactly as described, would stay again!"

"As advertised, had a great time!"

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

"It was alright "

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

"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. "

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

"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...

"This house has the perfect location to explore the town. We stayed in this house for the St. Michael’s Running Festival and it couldn’t have been better. The location was so close to the start/finish lines and there were so many restaurants within a few minutes walk. "

"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."