Photo by Assya A
Search Apartments in Chestertown
- Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Compare 90 Apartments in Chestertown with updated reviews, rates, and availability.

Bay View Studio Apartment
Bay View Studio Apartment
10.0 out of 10, Exceptional, (42)

Newly restored apartment in the heart of Chestertown
Newly restored apartment in the heart of Chestertown
9.8 out of 10, Exceptional, (21)

Historic Downtown Garden Oasis with Private Patio
Historic Downtown Garden Oasis with Private Patio
10.0 out of 10, Exceptional, (26)

Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
Cozy 2-bedroom apartment with WiFi, AC in charming Havre de Grace
The price is SAR 589
SAR 804 total
includes taxes & fees
29 Apr - 30 Apr

18th Cent. Charm in Historic Downtown Annapolis
18th Cent. Charm in Historic Downtown Annapolis
9.8 out of 10, Exceptional, (6)
The price is SAR 713
SAR 1,390 total
includes taxes & fees
18 Apr - 19 Apr

COZY DOWNTOWN APARTMENT-Naval Academy Vicinity
COZY DOWNTOWN APARTMENT-Naval Academy Vicinity
9.8 out of 10, Exceptional, (38)

Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
9.6 out of 10, Exceptional, (30)

'At Fells Point' CitySide - 'Tons better than a hotel!'
'At Fells Point' CitySide - 'Tons better than a hotel!'
9.8 out of 10, Exceptional, (187)
The price is SAR 330
SAR 763 total
includes taxes & fees
22 Apr - 23 Apr
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.
Save an average of 15% on thousands of hotels when you're signed in
Other property types in Chestertown

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
10.0 out of 10, Exceptional, (211)

Chesapeake Houseboat Getaway on Kent Island, Maryland
Chesapeake Houseboat Getaway on Kent Island, Maryland
9.8 out of 10, Exceptional, (23)
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.
Recent reviews of Chestertown hotels
Recent reviews of Chestertown hotels

Historic Inns of Annapolis
5/5 Excellent
"Charming to stay in a historic property so close to the State House and an easy walk to the City Dock"
A verified traveler stayed at Historic Inns of Annapolis
Posted 19 hours ago
Explore a world of travel with Expedia
Explore a world of travel with Expedia
Top Apartments in Other Destinations
More Accommodation Types in Chestertown
- Vacation Homes in Chestertown
- Cottages in Chestertown
- Guest Houses in Chestertown
- Motels in Chestertown
- RV Parks in Chestertown
- Houseboats in Chestertown
- B&B in Chestertown
- Farmstay in Chestertown
- Condo Rentals in Chestertown
- Cabin Rentals in Chestertown
- Villas in Chestertown
- Lodges in Chestertown
- Hotels