Chestertown, MD Apartments from SAR 470

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

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. Historic Downtown Garden Oasis with Private Patio : Free WiFi, outdoor space, and separate dining areas are included.

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

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Our top choices for Chestertown apartments

First Floor Studio Apartment in Historic Chestertown

Chestertown

Lisa v.

SAR 597 total

includes taxes & fees

22 Jul - 23 Jul

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

Millington

Riley B.

SAR 470 total

includes taxes & fees

27 Jul - 28 Jul

Cozy Fells Point Gem / In The Heart of Fells Point

Fells Point

Marie

SAR 850 total

includes taxes & fees

21 Jul - 22 Jul

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

Rock Hall

Tara K.

SAR 1,065 total

includes taxes & fees

17 Jul - 18 Jul

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

Greektown

Karen B.

SAR 859 total

includes taxes & fees

19 Jul - 20 Jul

1 bedroom, in-room safe, desk, iron/ironing board

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

Nottingham City

SAR 573 total

includes taxes & fees

20 Jul - 21 Jul

Waterfront Retreat with Private Dock and Beach

Worton

Jennifer W.

SAR 1,422 total

includes taxes & fees

19 Jul - 20 Jul

Turtle Cove Room

Kent County

SAR 703 total

includes taxes & fees

28 Jul - 29 Jul

Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace

Havre de Grace

Liza

SAR 1,011 total

includes taxes & fees

27 Jul - 28 Jul

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.

SAR 755 total

includes taxes & fees

28 Jul - 29 Jul

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

Aberdeen

Warren B.

SAR 800 total

includes taxes & fees

3 Aug - 4 Aug

Waterfront Oasis of Annapolis Star

Annapolis

Thomas

SAR 1,935 total

includes taxes & fees

19 Jul - 20 Jul

Coffee/tea maker, fridge, microwave, oven

Pool Loft Suite | Bay Access & Beach Passes

Cape Saint Claire

Ana S.

SAR 1,875 total

includes taxes & fees

1 Aug - 2 Aug

18th Cent. Charm in Historic Downtown Annapolis

Historic District

Maureens B.

SAR 1,631 total

includes taxes & fees

27 Jul - 28 Jul

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Top Chestertown Hotel Reviews

Comfort Inn & Suites Chestertown

10/10 Excellent

"We stayed there two nights for my daughter’s tournament. The room is clean and quiet, the breakfast is good. Highly recommended!"

Historic Inns of Annapolis

10/10 Excellent

"I loved the historic building- upgraded with 21stC amenities of course- like electricity and an elevator. Bed was very cozy. Bathroom window faced St. Mary's church and bedroom faced Capitol bldg. A short 2 block walk to a city owned parking garage, $24 for 24 hours. Not bad. And the restaurants all close by. I've been to Annapolis many times, but never overnight, so this was a great spot that my Lady absolutely adored!"

Best Western Plus Hotel & Conference Center

8/10 Good

"We booked the executive king Jacuzzi room. The room was clean very spacious. The Jacuzzi was a little difficult to get into with the steps. They felt a little slippery. The shower was built into the Jacuzzi so there was no curtain and water did sprinkle everywhere which made the floor slippery. We were a little disappointed. The pool was out of order. The hot tub was out of order due to a maintenance thing and we weren’t told until we went down to go swimming. The pool was one of the main reasons why we booked that particular hotel the breakfast was great. The restaurant was good the convenience store I couldn’t find and I have no idea where the comedy club was. If you drive there, there’s lots of restaurants and stores nearby. However, if you Uber or don’t have a car, we had to DoorDash anything we needed."

Frequently asked questions

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

There are plenty of places to stay in Chestertown with 44 hotels and other accommodations. Though there aren't many apartments, we can help you find similar accommodations. When you search on Expedia, you can use the filters to search for conveniences you might find in an apartment like a kitchen. Even filter by similar property types like vacation homes, condos, or cabins.

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?

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. Historic Downtown Garden Oasis with Private Patio: Free WiFi, outdoor space, and separate dining areas are included.

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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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chestertown apartments

First Floor Studio Apartment in Historic Chestertown

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

Cozy Fells Point Gem / In The Heart of Fells Point

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

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

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