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Our top choices for Chestertown vacation homes

Amazing Modern house with a full kitchen and parking

Amazing Modern house with a full kitchen and parking
Smyrna
9.2 out of 10, Wonderful, (10 reviews)
"The house is a beautiful place to stay. The location was ideal for going to attractions and stores. "
United States
Laurie S.
The price is AED 463
AED 1,060 total
includes taxes & fees
5 May - 6 May
Amazing Modern house with a full kitchen and parking

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 AED 918
AED 1,538 total
includes taxes & fees
1 May - 2 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, (43 reviews)
"We had a wonderful stay! The host was incredibly kind, responsive, and helpful throughout, making everything smooth and stress-free. The house itself was a great place to stay. It is clean, comfortable, and exactly as described. We really appreciated the thoughtful touches and would happily stay here again. Highly recommended!"
United States
Supriya V.
The price is AED 270
AED 921 total
includes taxes & fees
4 May - 5 May
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

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, (38 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 AED 496
AED 1,206 total
includes taxes & fees
3 May - 4 May
Large 2 bedroom house with private parking in a nice neighborhood

Adorable two-bedroom retreat close to Easton, Denton, Centreville

Adorable two-bedroom retreat close to Easton, Denton, Centreville
Queen Anne
10.0 out of 10, Exceptional, (28 reviews)
"Really cute little place - very clean and owners are great about checking in on you to make sure things are great."
United States
Cheryl
Adorable two-bedroom retreat close to Easton, Denton, Centreville

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 AED 643
AED 1,335 total
includes taxes & fees
4 May - 5 May
Bayside Cottage steps from Rock Hall Harbor

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 AED 426
AED 1,044 total
includes taxes & fees
6 May - 7 May
Boho Oasis 2 Bed 1 Bath home in Baltimore City!

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 AED 757
AED 1,530 total
includes taxes & fees
27 May - 28 May
Charming Coastal/Country Home w/3 Acres & Sauna!

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 AED 511
AED 666 total
includes taxes & fees
3 May - 4 May
Secluded Tiny Pool House -Private Pool -Self Check in

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, (151 reviews)
"Great house for a quick little getaway with family. The house is perfect for families with children; relaxed and friendly, not fussy. Would definitely recommend."
United States
Alison R.
The price is AED 889
AED 1,865 total
includes taxes & fees
5 May - 6 May
5-bedroom vacation home 5 minutes from historic Charlestown

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 AED 775
AED 1,942 total
includes taxes & fees
3 May - 4 May
Charming Pet-Friendly Stay - Near Bay & Beaches.

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 AED 349
AED 1,014 total
includes taxes & fees
2 May - 3 May
Hidden Fells Point Gem / Private Courtyard Patio

Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Cape Saint Claire
9.8 out of 10, Exceptional, (11 reviews)
"Enjoyed our stay- thank you!"
United States
KateriK
The price is AED 716
AED 2,290 total
includes taxes & fees
3 May - 4 May
Annapolis Home | Fenced Yard | Pool Table | 10 Guests

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (52 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is AED 735
AED 1,114 total
includes taxes & fees
6 May - 7 May
BAYSIDE BUNGALOW

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, (27 reviews)
"Clean, loved the sunroom!"
United States
Jamie C.
The price is AED 1,102
AED 1,419 total
includes taxes & fees
3 May - 4 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 AED 665
AED 2,567 total
includes taxes & fees
4 May - 5 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, (76 reviews)
"Parking availability and restaurant location"
United States
Sophie P.
The price is AED 771
AED 1,558 total
includes taxes & fees
5 May - 6 May
Cozy 2br home w/ parking in downtown Annapolis

Cozy Private Family Palace near BWI, Pet-Friendly

Cozy Private Family Palace near BWI, Pet-Friendly
Glen Burnie
9.8 out of 10, Exceptional, (24 reviews)
"Nice place and good location "
United States
FRANKLIN S.
Cozy Private Family Palace near BWI, Pet-Friendly

Cute, Cozy 2-bedroom house in near Annapolis with water access

Cute, Cozy 2-bedroom house in near Annapolis with water access
Herald Harbor
9.6 out of 10, Exceptional, (5 reviews)
The price is AED 317
AED 852 total
includes taxes & fees
4 May - 5 May
Cute, Cozy 2-bedroom house in near Annapolis with water access

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 property is lovely and the home is truly beautiful and comfortable. I highly recommend staying here; beautiful, peaceful--perfect."
United States
Jeffrey S.
The price is AED 815
AED 1,842 total
includes taxes & fees
3 May - 4 May
The Hideaway Spot- Waterfront w/ Dock on Long Cove
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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Top Chestertown Hotel Reviews

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