Compare Chestertown Apartments

Name: Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Price range: $286 total

Featured Apartments in Chestertown

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

$145 nightly

$154 total

Nov 2 - Nov 3

Total with taxes and fees

Guests staying at this apartment enjoy a hot tub, laundry facilities, and a garden.

WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

At this apartment, guests have access to a garden.

Kitchen

Free WiFi

Cozy Fells Point Gem / In The Heart of Fells Point

$197 nightly

$228 total

Oct 8 - Oct 9

Total with taxes and fees

This apartment is a smoke-free apartment building.

First Floor Studio Apartment in Historic Chestertown

$144 nightly

$159 total

Oct 12 - Oct 13

Total with taxes and fees

Guests of this apartment enjoy features like an outdoor pool, a gym, and laundry facilities. This golf apartment building also has barbecue grills.

Pool

Washer

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

At this apartment, guests have access to features like laundry facilities. This smoke-free apartment building also has a garden.

Walk to Shops & Dining from Dog-Friendly Apartment w Parking & Private Backyard

At this apartment, guests have access to features like laundry facilities. This smoke-free apartment building also has barbecue grills.

Newly restored apartment in the heart of Chestertown

$320 nightly

$353 total

Oct 8 - Oct 9

Total with taxes and fees

At this apartment, guests have access to features like laundry facilities.

Guests staying at this apartment enjoy a hot tub, laundry facilities, and barbecue grills. This smoke-free apartment building also has a garden.

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

$259 nightly

$286 total

Oct 8 - Oct 9

Total with taxes and fees

Guests staying at this apartment have access to laundry facilities, barbecue grills, and a garden.

Don't see what you're looking for?

See all available properties in Chestertown

View all properties

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotel Options in Chestertown

Red Roof Inn & Suites Chestertown

160 Scheeler Rd Chestertown MD

$72 nightly

$80 total

Oct 13 - Oct 14

Total with taxes and fees

The Lodge at Great Oak Landing

22170 Great Oak Landing Rd Chestertown MD

$124 nightly

$137 total

Oct 8 - Oct 9

Total with taxes and fees

Comfort Inn & Suites Chestertown

150 Scheeler Road Chestertown MD

$100 nightly

$111 total

Nov 1 - Nov 2

Total with taxes and fees

Apartments

Book apartments in Chestertown

Find your home-away-from-home when you book your next stay at an apartment in Chestertown. Apartments are ideal for families, groups of friends and even solo travelers. More space, more options and more freedom—apartments are short-term digs that feel like a long-term arrangement. From one-bedroom apartments to three bedrooms or more, Orbitz has an incredible selection to choose from. It’s never been easier to live like a local in Chestertown.

Apartments for everyone in Chestertown
Family apartments in Chestertown have plenty of room for everyone. You’ll find multiple bedrooms, laundry facilities and furnished living rooms, so you can have movie nights just like at home. Plus, hotels with kitchens cut down on time spent finding kid-friendly restaurants. Spend that time making memories instead.

Friends are the family you choose, but you don’t need to be too close this vacation. Luckily, you can book apartments even your pickiest pal will love. This getaway with the girls or guys doesn’t have to break the bank, either. Cheap apartments in Chestertown are just a click away. When it comes time to split the bill, no one will bail.

If you want the finer things in life, we’ll help you find luxury apartments in Chestertown faster than you can say “thousand thread count sheets.” Get your best sleep ever, then wake up with a freshly brewed espresso and a full breakfast. It’s just like home, only much, much better.

Whether you’re a bargain hunter or a luxury lover, kitchens and kitchenettes are one of the most important features of short-term apartments in Chestertown. It’s simple, really: Cooking your own meals is downright convenient. Even if you’re not a five-star chef, late-night snacks and morning mimosas get a whole lot easier when you’ve got a fully stocked kitchen to play with.

Chestertown Apartments essential information

Accommodation	74 Apartments
Lowest Price	$80
Highest Price	$353
Popular accommodation	WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL, WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD, Cozy Fells Point Gem / In The Heart of Fells Point, First Floor Studio Apartment in Historic Chestertown, Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace, Walk to Shops & Dining from Dog-Friendly Apartment w Parking & Private Backyard, Newly restored apartment in the heart of Chestertown, Bay View Studio Apartment, Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!