Chestertown Apartment Rentals from CA $174

Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA

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Our top choices for Chestertown apartments

First Floor Studio Apartment in Historic Chestertown

Chestertown

lesia k.

CA $222 total

includes taxes & fees

Jun 18 - Jun 19

Newly restored apartment in the heart of Chestertown

Chestertown

Anonymous traveller

CA $537 total

includes taxes & fees

Jun 14 - Jun 15

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

Rock Hall

Michael D.

CA $413 total

includes taxes & fees

Jun 14 - Jun 15

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

Millington

Riley B.

CA $174 total

includes taxes & fees

Jun 29 - Jun 30

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

Havre de Grace

Liza

CA $391 total

includes taxes & fees

Jun 16 - Jun 17

Cozy Fells Point Gem / In The Heart of Fells Point

Fells Point

Adrienne K.

CA $313 total

includes taxes & fees

Jun 15 - Jun 16

Turtle Cove Room

Kent County

CA $243 total

includes taxes & fees

Jul 6 - Jul 7

Waterfront Retreat with Private Dock and Beach

Worton

Jennifer W.

CA $528 total

includes taxes & fees

Jun 28 - Jun 29

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Top Chestertown Hotel Reviews

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

4/10 Poor

"The hotel is the worst hotel I have ever stayed in. The check in lady was beyond unprofessional from the first moment. Everything is super dirty and old. The only thing that was good was the breakfast. Good food and clean court. Otherwise I will never stay there again. Also charged me $25 for early checkin when the expedia email clearly stated the check in times. "

Annapolis Waterfront Hotel, Autograph Collection

6/10 Okay

"One elevator didn’t work and the other elevator was unreliable. The restaurant is closed. The hallway and rooms feel more like a 1970’s Best Western - well worn and not without a musty odor. The HVAC in room 518 is either off or cooling the room to 65 degrees (nothing in the middle). It’s an older property and ,other than scraping it, I don’t know how you could correct all of the issues."

Historic Inns of Annapolis

4/10 Poor

"The property is in a great location. Plenty to do in the area without having to drive. Unfortunately the staff are less than helpful. We checked out at 11am. At 12 noon, we realized we left a bag hanging from the bathroom door. Called, staff said they wou look into it. Took down my number and address. Called them back a few hours later and they claim no one turned in a bag. Hello, the cleaning staff was going in this room before the next guest at 4pm and the receptionist could have called the cleaning staff to grab it for us. Nope, I guess the receptionist job description doesn't include taking any initiative."

The Lodge at Great Oak Landing

4/10 Poor

"We left 1 hour after arrival... Enough said! This is very much a buyer beware situation. It's no resort. There was absolutely no food available. Tiki bar is permanently closed. Small restaurant was also closed and our only option was food from the front desk. It's about a 30 minute drive to the closest restaurant. The response from the front desk was simply "most restaurants around here are closed on Mondays and Tuesdays." That doesn't help a stranded traveler at your hotel. How does a resort not have any food available? HUGE red flag. The beach is hundreds of yards from the hotel with in and out access only available to hotel guests during office hours of 8:00 to 4:30. This is very much a marina first and a hotel second if not fifth. The staff was nonchalant & unwelcoming. The best decision we made truly was leaving."

Find out more about Chestertown

Chestertown Apartments information

Number of reviews	518
Accommodation	82 Apartments
Lowest Price	CA $174
Highest Price	CA $702

Frequently asked questions

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

There are plenty of places to stay in Chestertown with 43 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?

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, laundry facilities, and free WiFi. A fitness center and onsite laundry facilities are on site. Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat: Located 21.4 mi/34.4 km away in Pasadena. Free WiFi and Smart TVs are included. Access to an outdoor pool is available on site. Waterfront Oasis of Annapolis Star: Located in Annapolis, 25.8 mi/41.5 km away. Includes a private pool, free WiFi, and fireplaces. Access to an outdoor pool is available on site. WORLD'S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD: 16.1 mi/25.9 km away in Earleville. Free WiFi and Smart TVs are included. Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC: Located in Baltimore, 26.5 mi/42.7 km from Chestertown. Includes free WiFi, private patios, and Smart TVs. Access to onsite laundry facilities is available on site.

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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Treat yourself

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Check prices for these dates

Our top choices for Chestertown apartments

First Floor Studio Apartment in Historic Chestertown

Newly restored apartment in the heart of Chestertown

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

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

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

Cozy Fells Point Gem / In The Heart of Fells Point

Turtle Cove Room

Waterfront Retreat with Private Dock and Beach

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

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

Pool Loft Suite | Bay Access & Beach Passes

Waterfront Oasis of Annapolis Star

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

Beachcomber Suite

Home away from home with WiFi and AC in delightful Parkville

Find vacation rentals that suit your style

Top Chestertown Hotel Reviews

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

Annapolis Waterfront Hotel, Autograph Collection

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

Historic Inns of Annapolis

The Lodge at Great Oak Landing

Best Western Kent Narrows Inn

Hampton Inn Baltimore/White Marsh

Hyatt Place Kent Narrows & Marina

Quality Inn & Suites Bel Air I-95 Exit 77A

Find out more about Chestertown

Chestertown Apartments information

Frequently asked questions

Explore a world of travel with Expedia

Search Apartment Rentals in Chestertown

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

Newly restored apartment in the heart of Chestertown

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

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

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

Cozy Fells Point Gem / In The Heart of Fells Point

Turtle Cove Room

Waterfront Retreat with Private Dock and Beach

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

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

Pool Loft Suite | Bay Access & Beach Passes

Waterfront Oasis of Annapolis Star

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

Beachcomber Suite

Home away from home with WiFi and AC in delightful Parkville

Find vacation rentals that suit your style

Top Chestertown Hotel Reviews

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

Find out more about Chestertown

Chestertown Apartments information

Frequently asked questions

Explore a world of travel with Expedia