Chestertown Vacation Rentals
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Chestertown vacation homes
Vacation Home in Stevensville
Charming Coastal/Country Home w/3 Acres & Sauna!9.6 out of 10, Exceptional, (34 reviews)
"Great stay, would do it again."
Brandon D.
The price is CA $104
CA $356 total
includes taxes & fees
Mar 8 - Mar 9
Vacation Home in Arnold
Large 2 bedroom house with private parking in a nice neighborhood9.4 out of 10, Exceptional, (36 reviews)
"Super clean place, great communication from the host, and home is exactly as described and shown in pictures. "
Traci L.
The price is CA $172
CA $436 total
includes taxes & fees
Mar 12 - Mar 13
Vacation Home in Fells Point
Hidden Fells Point Gem / Private Courtyard Patio9.6 out of 10, Exceptional, (94 reviews)
"Lenny & his housekeeper Elviea were exceptionally helpful, funny and a delight to be with! I spent two weeks here & it was the best place I've ever stayed compared to my stays in Korea, Ireland & several other US cities.
Highly recommend!"
Edward J.
The price is CA $94
CA $294 total
includes taxes & fees
Mar 12 - Mar 13
Vacation Home in Grasonville
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.9.6 out of 10, Exceptional, (12 reviews)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
Joe C.
The price is CA $342
CA $577 total
includes taxes & fees
Mar 12 - Mar 13
Vacation Home in Stevensville
Relax on Kent Island in a 4 Bedroom Home w/Waterview!9.8 out of 10, Exceptional, (43 reviews)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
Stephanie S.
The price is CA $127
CA $382 total
includes taxes & fees
Mar 10 - Mar 11
Vacation Home in Smyrna
Amazing Modern house with a full kitchen and parking9.2 out of 10, Wonderful, (9 reviews)
"The house is a beautiful place to stay. The location was ideal for going to attractions and stores. "
Laurie S.
The price is CA $162
CA $387 total
includes taxes & fees
Mar 16 - Mar 17
Vacation Home in Berea
Boho Oasis 2 Bed 1 Bath home in Baltimore City!10.0 out of 10, Exceptional, (3 reviews)
"House kept very clean and neighborhood was really quiet at night! Will be staying again."
Pai’Syn
The price is CA $141
CA $365 total
includes taxes & fees
Mar 10 - Mar 11
Vacation Home in Perryville
5-bedroom vacation home 5 minutes from historic Charlestown9.8 out of 10, Exceptional, (148 reviews)
"Magical and made tons of family wedding memories. What a perfect house on the river!! We will be booking again"
Mary D.
The price is CA $353
CA $724 total
includes taxes & fees
Mar 5 - Mar 6
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.
Find vacation rentals that suit your style
Private vacation homes
Cottages
Save an average of 15% on thousands of hotels when you're signed in
Top Chestertown Hotel Reviews
Americas Best Value Inn Edgewood
10/10 Excellent
Find out more about Chestertown
Chestertown Vacation Homes information
Number of reviews | 509 |
|---|---|
Accommodation | 486 Vacation Homes |
Lowest Price | CA $127 |
Highest Price | CA $1,652 |
Explore a world of travel with Expedia
- Best Western Hotels in Aberdeen Proving Ground
- Aberdeen Proving Ground Hotels
- Apartments in Betterton
- Hotels near Betterton Beach
- Cottages in Betterton
- Betterton Hotels
- Resorts in Betterton
- Cecilton Hotels
- Farmstay in Centreville
- Chalets in Centreville
- Boutique Hotels in Centreville
- Centreville Hotels
- Inns in Centreville
- Cheap Hotels in Church Hill
- Hotels with Hot Tubs in Church Hill
- Church Hill Hotels
- Inns in Church Hill
- Earleville Hotels
- Hotels near Eastern Neck National Wildlife Refuge
- Romantic Hotels in Edgewood
- Edgewood Hotels
- B&B in Galena
- Hotels with Hot Tubs in Galena
- Romantic Hotels in Galena
- Galena Hotels
- Lodges in Galena
- Motels in Galena
- Resorts in Galena
- Independent Hotels in Georgetown
- Rv Parks in Georgetown
- Villas in Georgetown
- Guest Houses in Great Oak Landing
- Great Oak Landing Hotels
- Rv Parks in Great Oak Landing
- Hotels near Gunpowder Falls State Park
- Lodges in Kennedyville
- B&B in Massey
- Massey Hotels
- Lodges in Massey
- Motels in Massey
- Millington Hotels
- Hotels near Phillips Army Airfield
- Pomona Hotels
- Vacation Homes in Pomona
- Apartments in Queen Anne's County
- B&B in Queen Anne's County
- Boutique Hotels in Queenstown
- Hotels with a Pool in Queenstown
- Luxury Hotels in Queenstown
- Spa Hotels in Queenstown
- Queenstown Hotels
- B&B in Rock Hall
- Hotels near Rock Hall Harbor
- Beach Hotel Hotels in Rock Hall
- Cheap Hotels in Rock Hall
- Oceanfront Hotels in Rock Hall
- Rock Hall Hotels
- Motels in Rock Hall
- Still Pond Hotels
- Lodges in Still Pond
- Villas in Still Pond
- Farmstay in Tolchester Beach
- Hotels near Washington College
- B&B in White Crystal Beach
- Cottages in White Crystal Beach
- White Crystal Beach Hotels
- Resorts in White Crystal Beach
- Worton Hotels
- Flights from Phillips Army Airfield
- Flights from Edgewood
- Flights from Gunpowder
- Flights from Kennedyville
- Flights from Massey
- Flights from Barclay
- Flights from Aberdeen Proving Ground
- Flights from Centreville
- Flights from Birmingham (BHX) to Aberdeen (APG)
- Flights from Boston (BOS) to Aberdeen (APG)
- Flights from Brussels (BRU) to Aberdeen (APG)
- Flights from Cambridge (CGE) to Aberdeen (APG)
- Flights from Charlotte (CLT) to Aberdeen (APG)
- Flights from Copenhagen (CPH) to Aberdeen (APG)
- Flights from Dover (DOV) to Aberdeen (APG)
- Flights from Detroit (DTW) to Aberdeen (APG)
- Flights from Hamburg (HAM) to Aberdeen (APG)
- Flights from Indianapolis (IND) to Aberdeen (APG)
- Flights from Kingston (KIN) to Aberdeen (APG)
- Flights from Minneapolis (MSP) to Aberdeen (APG)
- Flights from Princeton (PCT) to Aberdeen (APG)
- Flights from Philadelphia (PHL) to Aberdeen (APG)