
Apartment holiday rentals in Dorchester County
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Top-rated apartment rentals in Dorchester County
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ALL INCLUDED- Chic Move in Ready
Convenient for working on a boat in Oxford. Less expensive than staying in Oxford.

2nd floor studio apartment
We had a great stay. Would highly recommend to anyone, especially those doing Ironman races. Full kitchen and plenty of space!

Private apt above garage w/ pier and water access
We had an amazing stay at this Airbnb during the GFNY cycling event in Cambridge, MD. The property was spotless and located just about a mile from the event site, which made getting to and from the race incredibly easy. The quiet neighborhood and proximity to the water provided a peaceful and relaxing atmosphere—perfect for unwinding before and after the event. The two-bedroom unit was fully stocked with everything we needed, and the beds were extremely comfortable. Jason was incredibly accommodating, even allowing us a late check-out to fit our event schedule, which was a huge help. I would highly recommend this place to anyone visiting the area, whether for an event or just to enjoy a quiet getaway. We’ll definitely stay here again!

Historic St. Mary's City, MD
Our second time here! An absolutely adorable gem of an Airbnb with the nicest hosts and most beautiful garden and dock on the River! Great restaurant recommendations, super comfortable beds, and lovely living room. Perfect for families visiting the beloved St. Mary’s River.

Little Slice of Cambridge. Newly listed, 2 bedroom
We rented A Little Slice of Cambridge because of the Iron Man competition held that weekend. It was convenient to the venue...and allowed to walk to the competition and nearby restaurants. Pamela was a wonderful host...communicating easily. The rental was well stocked with toiletries, dishes, pots and pans and extras. The house was comfy and the beds comfortable. An enjoyable stay...unfortunately, we weren't able to stay for more sightseeing...although I did walk down to the Lighthouse and beautiful wharf.

Morning Light Apartment
Mary's place was everything we could've asked for. It had a well stocked kitchen, comfy bed, and nice shower. She was very communicative and we would love to stay again.

Eden Farm: Private Studio Minutes from Salisbury
Our stay was lovely! The property is quiet and peaceful. The apartment is right above the roosters so we could hear them crow every morning, but it didn't bother us. The parking is a bit of a walk from the apartment, but everything was clearly labeled and easy to find. The kitchen had basic pots and pans, plates and bowls, and utensils. But did not have things like cooking oil, salt/pepper, etc. It didn't hinder our stay, but these are mentioned in the listing, so it was noted. Overall, we enjoyed our stay!

Church Creek Natures' Rest
This place was so clean and comfortable. The deck was very quiet and private. The entire place was very accommodating. The beds were so comfy that it was hard to get motivated in the mornings….lol. The local Rise Up coffee was a special touch. It is one of my favorite places to get coffee when I’m in the Cambridge area. I had two other quest with me and they too agree that the place was delightful. The steps going up to the apartment were a bit difficult for my 77 year old mother but other than that we had a wonderful visit. I would highly recommend Kara’s place. Thank you again!
Private apartment rentals

The Sailboat one bedroom
Had a great stay at Al’s place. 2 minutes from the BHE site I was working at. Would definitely stay again.

SUPER WATER-VIEW 1 BEDROOM APT/CAMBRIDGE MARYLAND
Larry's place was perfect. We were able to book with him last minute for the Eagleman and he was able to accommodate our needs. It was a pleasure to meet Larry and have him give us a tour of the home. He was a great host. Would recommend to anyone!

Cambridge Apt in Walkable Neighborhood
GREAT location within short time/distance for activities, dining and sites. The waterfront and near marina location made for beautiful, quiet walks and sunrises. Space itself set up well for time spent relaxing, cooking and sleeping; comfortable bedding, workable kitchen/dining area, A/C and ceiling fans located well to keep entire apartment comfortable. Would definitely stay here again!

Furnished Very Spacious
Vanessa was extremely helpful and the apartment was very comfortable and clean.

Chesapeake bay view
Family-friendly apartment rentals

Cozy 3rd Floor Apartment in Historic West End
We actually ended up staying at another property of Mary’s because of a boiler issue at the original place. Mary got in touch immediately & offered an upgrade for the price of our original stay. She made sure we got everything we needed, sending over supplies & solving an issue with the tv. A super responsive host and we much appreciated that! The place we ended up at was right on the Choptank River with gorgeous views and even ducks to feed!!! (Mary supplied the duck food!) A great, relaxing stay!!

Private apt above garage w/ pier and water access
We had an amazing stay at this Airbnb during the GFNY cycling event in Cambridge, MD. The property was spotless and located just about a mile from the event site, which made getting to and from the race incredibly easy. The quiet neighborhood and proximity to the water provided a peaceful and relaxing atmosphere—perfect for unwinding before and after the event. The two-bedroom unit was fully stocked with everything we needed, and the beds were extremely comfortable. Jason was incredibly accommodating, even allowing us a late check-out to fit our event schedule, which was a huge help. I would highly recommend this place to anyone visiting the area, whether for an event or just to enjoy a quiet getaway. We’ll definitely stay here again!

Turn of the Century Gracious Living
Lovely & comfortable space in a charming town. Mary was so helpful and easy to get a hold of. Great, great find.

Historic St. Mary's City, MD
Our second time here! An absolutely adorable gem of an Airbnb with the nicest hosts and most beautiful garden and dock on the River! Great restaurant recommendations, super comfortable beds, and lovely living room. Perfect for families visiting the beloved St. Mary’s River.
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- Sandy Point State Park
- Maryland Renaissance Festival
- Heritage Shores
- Quiet Waters Park
- Flounder Pavilion Beach Front - Sandy Point State Park
- Ragged Point Beach
- Plantation Lakes Golf and Country Club
- Breezy Point Beach & Campground
- Gerry Boyle Park
- Brownies Beach
- Idlewilde Restoration Project
- Chesapeake Beach Water Park
- Oxford Beach
- Rose Haven Memorial Park
- Quiet Waters Dog Beach
- Six Flags America
- Matapeake Clubhouse and Beach
- Guard Shore
- Piney Point Beach
- Lane Beach
- Bayfront Beach
- North Beach Boardwalk/Beach
- Sandyland Beach
- Franklin Manor Community Private Park