Search Apartments in Eastern Shore

Change your mind

Book hotels with free cancellation

Treat yourself

Be picky

Search almost a million properties worldwide

Check prices for these dates

In two weeks

In one month

In two months

In three months

Featured Apartments in Eastern Shore and around

Our top choices for Eastern Shore apartments

"Check in was easy, parking was available and the staff were very helpful!"

Deluxe Apartment, 2 Bedrooms, Kitchen, City View (Shared Balcony, A02) | Living room

"I have stayed here for several years now. The property is located in a great spot. The rooms are clean but could use updating. All and all it is well worth the money"

includes taxes & fees

25 Aug - 26 Aug

Deluxe Apartment, 4 Bedrooms, City View (No Topsheet / Towels / Paper Products) | In-room dining

"Location was perfect for our weekend at the beach."

includes taxes & fees

8 Sept - 9 Sept

"The stay was perfect, so close to the beach, clean and exactly what we needed. "

"Property was in a great location. Check in and check out was easy. Having a hot tub and deck with table and chairs was nice. Unit was clean with an exception of the floors. I can understand it being a little sandy because of being at the beach, but there were tortilla chips in several areas of the floor. "

includes taxes & fees

11 Sept - 12 Sept

"Excellent apartment , fantastic location , 1 min from the boardwalk, great customer service. "

"Stayed for the weekend- parked the car and could walk to everything- perfect. Host was super responsive and the place was super clean!"

"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "

includes taxes & fees

2 Sept - 3 Sept

Fridge, microwave, coffee/tea maker, toaster

"The room and location were perfect. Very clean and comfortable space to stay and right in the heart of town. "

"Rude. Canceled our reservation because they don’t want to follow the terms they agreed upon with Expedia. I selected pay at the hotel, attempted to bill me without my permission. Then canceled my reservation. More worried about shaking people down for money than their guest experience. "

includes taxes & fees

22 Sept - 23 Sept

"A great long weekend stay. The pictures are very representative of the unit; it's clear there was a recent renovation and everything was clean when we arrived. Fantastic location one block from beach/boardwalk, and it was great not having to cross the larger roadways to get there. The owner was very responsive with questions I had in advance of booking. Only suggestion would be a dresser would be nice to have, but was not a concern for us since we were only there a few days. Overall though, we...

"Great time"

"Great experience! "

"Close to the beach, restaurants and mini golf, alley oops, great location."

"Clean, quiet and had everything I needed"

"Lovely place to stay in downtown Chestertown. So close to walk to eating, shopping and events. Had many great amenities to make the stay comfortable. Host was very communicative and quick to respond. "

"The listing for this property failed to mention that it was a multiple unit building, with tons of STEPS & NO PARKING not till after we paid and confirmed was the parking made know. I would have never booked this traveling with kids to go to the beach having to carry everything up and down 26 steps multiple times a day. There was no place to put anything the closet was useless the shelf was too low to use the hangers, the door would not fully open either. In the bathroom the shower head either...