Chester apartments
We found 11 apartments — enter your dates for availability
Explore Chester condo rentals

Cozy Waterfront Apartment Chester, MD
Sleeps 2 · 1 bedroom · 1 bathroom

Kent Island Waterfront Cottage
Sleeps 6 · 2 bedrooms · 1 bathroom

Serene Waterfront Apartment on Kent Island
Sleeps 2 · 1 bedroom · 1 bathroom

Quiet Waterfront Getaway Private Escape 1BR Apt Retreat with Optional Boat Dock
Sleeps 4 · 1 bedroom · 1 bathroom

Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
Sleeps 5 · 3 bedrooms · 1 bathroom

Annapolis Spa Retreat, Sauna, Jacuzzi, King Bed Couples Quiet Loft Apt. Getaway
Sleeps 4 · 1 bedroom · 1 bathroom
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- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
What's it like to stay at an apartment in Chester?
You'll find 9 lodging options in Chester. Though there aren't many apartments, we can help you find accommodation that is similar. When you search for a place to stay on Expedia, you can filter by amenities such as a kitchen— one of the conveniences often found in an apartment. You can also search for similar properties such as holiday homes, condos or cabins.
How do you know if an apartment is a good option for you?
Often offering more space than a traditional hotel room, an apartment comes with a kitchen, so you can cook some of your meals. Apartments are ideal for families who want the conveniences of home, and also for solo travellers who want to stay in a quieter area.
What will the weather be like when I travel to Chester?
Although weather is just one factor, it can really affect your travel plans, especially if you're planning an extended stay in Chester. The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chester is 1414 mm.
What should I see in Chester?
Explore the area and family-friendly sights such as Annapolis Maritime Museum, or get out into nature at a spot like Northern Chesapeake Bay. In the wider area, you'll find Matapeake State Park and Eastern Neck National Wildlife Refuge.
What's the best way to get to and around Chester?
Knowing a bit about the transportation options can save you time when you get to your destination. Fly into Easton, MD (ESN-Easton - Newnam), which is located 16.6 mi (26.7 km) away from the heart of the city. Otherwise, you can search for flights to Baltimore Washington International Airport (BWI), which is 24.8 mi (39.9 km) away. If you'd like to venture out around the area, you may want a rental car for your journey.
