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Our top choices for Chestertown holiday homes

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (12 reviews)
"Great overnight stay for a wedding nearby. Would highly recommend!"
United States
Kevin F.
The price is £315
includes taxes & fees
18 May - 19 May
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (44 reviews)
"The place was perfect, exactly as depicted, in a lovely home in a quiet area a block from bay. It was convenient to most of Kent. The rooms are lovely and cozy with additional pullout on lower floors. I have teens so the added space was a blessing. The host was very kind and attentive checking in and offering any information to make our stay more pleasant. Checking in and out was simple and care free. I would certainly recommend it and intend to stay there again."
United States
Brian
The price is £189
includes taxes & fees
17 May - 18 May
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
8.0 out of 10, Very good, (15 reviews)
"Met our needs. Great stay."
United States
Robert C.
The price is £72
includes taxes & fees
18 May - 19 May
Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.6 out of 10, Exceptional, (35 reviews)
"Great stay, would do it again."
United States
Brandon D.
The price is £280
includes taxes & fees
27 May - 28 May
Charming Coastal/Country Home w/3 Acres & Sauna!

Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (2 reviews)
"Property was nicely refurbished and furnished and well equipped. The younger set especially enjoyed the 5 bikes in good condition and the large yard to play sports. All in all, a great weekend stay!"
United States
Dorothy R.
The price is £274
includes taxes & fees
2 Jun - 3 Jun
Bayside Cottage steps from Rock Hall Harbor

Large 2 bedroom house with private parking in a nice neighborhood

Large 2 bedroom house with private parking in a nice neighborhood
Arnold
9.4 out of 10, Exceptional, (40 reviews)
"Super clean place, great communication from the host, and home is exactly as described and shown in pictures. "
United States
Traci L.
The price is £252
includes taxes & fees
17 May - 18 May
Large 2 bedroom house with private parking in a nice neighborhood

Hidden Fells Point Gem / Private Courtyard Patio

Hidden Fells Point Gem / Private Courtyard Patio
Fells Point
9.6 out of 10, Exceptional, (95 reviews)
"Awesome place, great location"
United States
Mark M.
The price is £168
includes taxes & fees
19 May - 20 May
Hidden Fells Point Gem / Private Courtyard Patio

Charming Pet-Friendly Stay - Near Bay & Beaches.

Charming Pet-Friendly Stay - Near Bay & Beaches.
Annapolis
10.0 out of 10, Exceptional, (7 reviews)
"Very clean and very convenient location for our trip. "
United States
Greg S.
The price is £392
includes taxes & fees
18 May - 19 May
Charming Pet-Friendly Stay - Near Bay & Beaches.

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (54 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is £226
includes taxes & fees
18 May - 19 May
BAYSIDE BUNGALOW

Boho Oasis 2 Bed 1 Bath home in Baltimore City!

Boho Oasis 2 Bed 1 Bath home in Baltimore City!
Berea
9.8 out of 10, Exceptional, (6 reviews)
"House kept very clean and neighborhood was really quiet at night! Will be staying again."
United States
Pai’Syn
The price is £227
includes taxes & fees
4 Jun - 5 Jun
Boho Oasis 2 Bed 1 Bath home in Baltimore City!

5-bedroom vacation home 5 minutes from historic Charlestown

5-bedroom vacation home 5 minutes from historic Charlestown
Perryville
9.8 out of 10, Exceptional, (152 reviews)
"This is the second time my group of friends has stayed here. The house is very comfortable and well-appointed, and the view is gorgeous! "
United States
Melinda S.
The price is £400
includes taxes & fees
19 May - 20 May
5-bedroom vacation home 5 minutes from historic Charlestown

Secluded Tiny Pool House -Private Pool -Self Check in

Secluded Tiny Pool House -Private Pool -Self Check in
Glen Burnie
8.6 out of 10, Excellent, (11 reviews)
"Jordan was a great host and communicated in a timely and professional manner. Outdoor space and pool were lovely for the hot sunny weekend. "
United States
Ellie F.
The price is £143
includes taxes & fees
17 May - 18 May
Secluded Tiny Pool House -Private Pool -Self Check in

Family-friendly home in Baltimore with WiFi, AC, Pool table, Washer & dryer

Family-friendly home in Baltimore with WiFi, AC, Pool table, Washer & dryer
Berea
9.8 out of 10, Exceptional, (6 reviews)
"Amazing house"
United States
Janell W.
The price is £163
includes taxes & fees
17 May - 18 May
Family-friendly home in Baltimore with WiFi, AC, Pool table, Washer & dryer

Glen Burnie Escape - Pet friendly with easy access to multiple attractions.

Glen Burnie Escape - Pet friendly with easy access to multiple attractions.
Glen Burnie
10.0 out of 10, Exceptional, (28 reviews)
"While the pictures are good, it truly doesn’t do the place justice. It was such a great stay! Very comfortable, very spacious. I feel like the owner did really great with it! "
United States
Danielle D.
The price is £287
includes taxes & fees
28 May - 29 May
Glen Burnie Escape - Pet friendly with easy access to multiple attractions.

Historic Row Home | Hot Tub - 1 Block from Gate 1!

Historic Row Home | Hot Tub - 1 Block from Gate 1!
Historic District
9.8 out of 10, Exceptional, (6 reviews)
"Perfect location. Very clean. Had everything we needed and front porch swing was a nice bonus. Would stay here every visit! "
United States
Tracie B.
The price is £530
includes taxes & fees
27 May - 28 May
Historic Row Home | Hot Tub - 1 Block from Gate 1!

Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (79 reviews)
"Parking availability and restaurant location"
United States
Sophie P.
The price is £331
includes taxes & fees
1 Jun - 2 Jun
Cozy 2br home w/ parking in downtown Annapolis

Spacious Private 2BR Suite in Abingdon with Separate Entrance

Spacious Private 2BR Suite in Abingdon with Separate Entrance
Bel Air South
The price is £106
includes taxes & fees
18 May - 19 May
Spacious Private 2BR Suite in Abingdon with Separate Entrance

The Hideaway Spot- Waterfront w/ Dock on Long Cove

The Hideaway Spot- Waterfront w/ Dock on Long Cove
Glen Burnie
9.0 out of 10, Wonderful, (11 reviews)
"THE PERFECT WATERSIDE GETAWAY!!! The Hideaway Spot is a true GEM of a location/property for "
United States
Karen M.
The price is £372
includes taxes & fees
18 May - 19 May
The Hideaway Spot- Waterfront w/ Dock on Long Cove

Abingdon Haven Hideaway

Abingdon Haven Hideaway
Abingdon
7.0 out of 10, Good, (2 reviews)
"We made good use of this rental, it was convenient to all our family & activities. Host is very kind & quickly helpful on request. The main problem with a basement apt is that the thermostat is usually upstairs in the main house, but host was most accommodating about temperature control. We rested well here and had a nice week."
United States
Pam L.
The price is £287
includes taxes & fees
19 May - 20 May
Abingdon Haven Hideaway
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.
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Chestertown Holiday Homes information

Number of reviews
599
Accommodation
489 Holiday Homes
Lowest Price
£72
Highest Price
£530