Serviced Apartments in Chestertown

More than just hotels
Apartments, cabins, holiday rentals and more, plus millions of reviews from Aussie & Kiwi travellers

Flexibility matters
24/7 support, so you can book with confidence

Unlock member prices with Mates Rates
You could save 10% or more on over 100,000 hotels right now.

Featured Apartments in Chestertown

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

Aberdeen MD

AU$267

1 Oct - 2 Oct

includes taxes & fees

WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL: Apartments with free WiFi and 1 hot tub.

Hot tub

Kitchen

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

Earleville MD

WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD: Beach apartments with free WiFi and parking. Located on the waterfront.

Kitchen

Free WiFi

First Floor Studio Apartment in Historic Chestertown

Chestertown MD

AU$229

1 Oct - 2 Oct

includes taxes & fees

First Floor Studio Apartment in Historic Chestertown: Golf apartments with free WiFi and an outdoor pool. Located next to a golf course.

Pool

Washing machine

Cozy Fells Point Gem / In The Heart of Fells Point

Baltimore MD

AU$335

4 Oct - 5 Oct

includes taxes & fees

Cozy Fells Point Gem / In The Heart of Fells Point: Apartments with free WiFi and parking. Located in the city centre.

Kitchen

Free WiFi

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

Havre de Grace MD

Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace: Apartments with free WiFi and parking.

Kitchen

Washing machine

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

Annapolis MD

Walk to Shops & Dining from Dog-Friendly Apartment w Parking & Private Backyard: Pet-friendly apartments with free WiFi and parking.

Kitchen

Washing machine

Bay View Studio Apartment

Annapolis MD

Bay View Studio Apartment: Apartments with free WiFi and 1 hot tub. Located on the waterfront.

Hot tub

Kitchen

Pool Loft Suite | Bay Access & Beach Passes

Annapolis MD

AU$714

5 Oct - 6 Oct

includes taxes & fees

Pool Loft Suite | Bay Access & Beach Passes: Family-friendly apartments with WiFi and parking.

Pool

Kitchen

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

Rock Hall MD

AU$403

4 Oct - 5 Oct

includes taxes & fees

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!: Apartments with free WiFi and parking.

Kitchen

Washing machine

2nd floor Spacious Downtown Getaway- Across from US Naval Academy

Annapolis MD

2nd floor Spacious Downtown Getaway- Across from US Naval Academy: Apartments with free WiFi and laundry facilities. Located in the city centre.

Kitchen

Washing machine

Historic Downtown Garden Oasis with Private Patio

Chestertown MD

Historic Downtown Garden Oasis with Private Patio: Apartments with free WiFi and parking. Located in the city centre.

Kitchen

Free WiFi

Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!

Annapolis MD

Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!: Family-friendly apartments with free WiFi and a fitness centre. Located in the city centre.

Kitchen

Washing machine

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.

Chestertown Apartments essential information

Accommodation	78 Apartments
Lowest Price	AU$114
Highest Price	AU$809
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, First Floor Studio Apartment in Historic Chestertown, Cozy Fells Point Gem / In The Heart of Fells Point, Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace, Walk to Shops & Dining from Dog-Friendly Apartment w Parking & Private Backyard, Bay View Studio Apartment, Pool Loft Suite \| Bay Access & Beach Passes, Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!, 2nd floor Spacious Downtown Getaway- Across from US Naval Academy, Historic Downtown Garden Oasis with Private Patio, Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!