Best Apartments in Chestertown for Your Vacation from ￥19,772

An aerial view of a town with a river, buildings, and surrounding greenery.

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Our top choices for Chestertown apartments

A house with a swimming pool, surrounded by a fence, and two red umbrellas.

1. First Floor Studio Apartment in Historic Chestertown

Chestertown

John R.

￥25,110 total

includes taxes & fees

Oct 19 - Oct 20

A spacious living area with a dining table, sofa, and a kitchen in the background.

2. Newly restored apartment in the heart of Chestertown

Chestertown

Susan A.

￥55,834 total

includes taxes & fees

Oct 25 - Oct 26

A living room with a fireplace, patterned furniture, a coffee table, and a bookshelf.

3. Secluded Cottage in Middle of Chestertown

Chestertown

Amy D.

￥43,310 total

includes taxes & fees

Oct 25 - Oct 26

A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.

4. Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Rock Hall

lisa p.

￥45,172 total

includes taxes & fees

Oct 17 - Oct 18

A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

5. Guest Suite for up to 2 in a Victorian on the Chester River

Millington

Riley B.

￥19,772 total

includes taxes & fees

Oct 19 - Oct 20

A covered porch with a wooden floor, a sofa with cushions, a ceiling fan, and a view of a green landscape.

6. Beachcomber Suite

Kent County

"We absolutely loved staying at the Beachcomber Suite. Tucked away off the main road, with a massive screened porch to enjoy the country side and gardens. It was cosy, clean, well appointed. The shower was amazing. We had a multi-course dinner at Sassafras on the water which was right up the road, 3 minutes away on the water front. I got a text from Jane and Dennis that evening if I wanted fresh bagels in the morning. Well, of course I do! They were warm multi seed and fantastic start to...

Lisa E.

￥33,836 total

includes taxes & fees

Nov 9 - Nov 10

A bedroom with a wooden headboard, striped pillows, a turtle-shaped pillow, and wall-mounted lamps.

7. Turtle Cove Room

Kent County

￥31,433 total

includes taxes & fees

Nov 9 - Nov 10

A fire pit with flames, surrounded by a metal frame, overlooking a body of water with a dock and trees in the background.

8. WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL

Aberdeen

Matthew

￥24,297 total

includes taxes & fees

Nov 11 - Nov 12

A waterfront with docked boats, a water taxi, and historic buildings.

9. Cozy Fells Point Gem / In The Heart of Fells Point

Fells Point

Carol

￥36,339 total

includes taxes & fees

Oct 28 - Oct 29

A bed with a dark headboard, a mirror, a potted plant, and a snack basket on the bedside table.

10. Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals

Nottingham City

"At the end of a multi-city trip filled with mixed hotel experiences, this stay was a true breath of fresh air. Everything was spotlessly clean, beautifully organized, and exactly as pictured. What truly set it apart were the thoughtful touches throughout the space—it was clear our host anticipated our every need, which even saved us an extra trip to the store! Parking was effortless, and the location made getting into the city by car or public transit super easy. Communication with our host was...

Jennifer R.

￥30,676 total

includes taxes & fees

Oct 27 - Oct 28

Stylish kitchen with open layout and island seating

11. Pool Loft Suite | Bay Access & Beach Passes

Cape Saint Claire

Ana S.

￥76,168 total

includes taxes & fees

Oct 18 - Oct 19

A spacious hallway with a staircase, a seating area with a sofa and armchairs, and a large window with a stained glass design.

12. Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC

Greektown

Rosa E.

￥39,437 total

includes taxes & fees

Oct 18 - Oct 19

A kitchen with a wooden countertop, a stove, and a refrigerator.

13. 18th Cent. Charm in Historic Downtown Annapolis

Historic District

Maureens B.

￥66,705 total

includes taxes & fees

Oct 18 - Oct 19

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Top Chestertown Hotel Reviews

The Inn at Chesapeake Bay Beach Club

10/10 Excellent

"The staff was awesome. Very professional and helpful. Our room was cleaned and well maintained. The food was great and the spa service was awesome as well."

Historic Inns of Annapolis

10/10 Excellent

"The convenience to downtown was the biggest plus for me. The Maryland Inn is on Main street so shopping and dining are an easy walk. I was in town for the Annapolis boat show so walking to and from the show was a fairly easy commute. The hotel was very clean, my room was well maintained each day. The only issue I had was the TV was not working but upon notification, it was fixed right away. Otherwise I'd say the only other thing that visitors will be surprised with is Check in is located at another hotel (all tied to same company), so there is a short walk to this property if you are getting dropped off. Overall impression - This is an OLD historic building and hotel - actually a meeting spot for the Annapolis Ghost Tours :-). So set your expectations for that, it is not an upscale, modern resort hotel experience. For me, it was perfect, and much better than some of the rental houses I've stayed in over the years. If you're excited about historic places and buildings, this will be a great experience for you."

Country Inn & Suites by Radisson, Baltimore North, MD

8/10 Good

"Our stay was quite un eventful and very restful with the following exception; I had checked the wrong date on the arrival and called Expedia to correct it which they said they would do, then beyond that my brother in law passed away and we had to leave a day early, which the hotel was very understanding and only charged for the nights we stayed. BUT Expedia has not refunded any of the excessive charges for either of the two nights involved. They sent a letter saying the hotel would not accept refunding the two nights, which is completely not true as I have a copy of the bill from the hotel and it only covers the two nights we actually spent. At this time I can never trust Expedia again to book anything!"

Find out more about Chestertown

Chestertown Apartments information

Number of reviews	362
Accommodation	77 Apartments
Lowest Price	￥19,772
Highest Price	￥76,168

Frequently asked questions

What's it like to stay at an apartment in Chestertown?

You can choose from 5 apartments in Chestertown for your vacation.

Why should you consider apartments instead of traditional hotels?

An apartment comes equipped with a kitchen, so you can cook some of your meals, and usually is more spacious than a traditional hotel room. Apartments are a good option for solo travelers who want to live like locals, and also for families wanting the conveniences of home.

What's the top apartment for my stay in Chestertown?

Here are some of the more popular apartments in the area to choose from: First Floor Studio Apartment in Historic Chestertown: Includes a private pool, free WiFi, and private patios. A fitness center and onsite laundry facilities are on site. WORLD'S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD: Located 16.1 mi/25.9 km away in Earleville. Free WiFi and Smart TVs are included. WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL: Located in Aberdeen, 18.4 mi/29.5 km away. Includes free WiFi, private patios, and Smart TVs. Onsite laundry facilities and a hot tub are on site. Cozy Fells Point Gem / In The Heart of Fells Point: It's located in Baltimore, 28.3 mi/45.5 km from Chestertown. Includes free WiFi and Smart TVs.

How many apartments can I expect to find in Chestertown?

Expedia has 5 apartments to book in Chestertown.

What can I expect from the weather during my trip to Chestertown?

Weather is only one factor, but it can really affect your travel plans, especially when you're planning an extended stay in Chestertown. The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.

What should I see and do in Chestertown?

Cultural attractions include Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater, whereas Northern Chesapeake Bay and Chesapeake Bay are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Chestertown Historic District and Rolphs Wharf Marina.

What's the best way to get to and around Chestertown?

Knowing a bit about the transportation options can make your trip smoother when you get to your destination. Fly into Baltimore, MD (MTN-Martin State), which is located 20.3 mi (32.7 km) from the heart of the city. Otherwise, you can search for flights to Easton, MD (ESN-Easton - Newnam), which is 28.2 mi (45.3 km) away. If you'd like to explore around the area, consider renting a car to take in more sights.

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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chestertown apartments

1. First Floor Studio Apartment in Historic Chestertown

2. Newly restored apartment in the heart of Chestertown

3. Secluded Cottage in Middle of Chestertown

4. Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!