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Our top choices for Chestertown vacation homes

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
The price is ¥24,289
¥49,821 total
includes taxes & fees
May 10 - May 11
Adorable two-bedroom retreat close to Easton, Denton, Centreville

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 ¥28,114
¥59,792 total
includes taxes & fees
Jun 1 - Jun 2
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

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 ¥39,080
¥65,451 total
includes taxes & fees
May 11 - May 12
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

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 ¥10,552
¥14,499 total
includes taxes & fees
May 19 - May 20
Charming 2-bedroom house in Aberdeen with WiFi and AC

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 ¥21,103
¥51,323 total
includes taxes & fees
May 11 - May 12
Large 2 bedroom house with private parking in a nice neighborhood

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 ¥30,500
¥62,653 total
includes taxes & fees
May 27 - May 28
Charming Coastal/Country Home w/3 Acres & Sauna!

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 ¥18,149
¥44,073 total
includes taxes & fees
May 11 - May 12
Boho Oasis 2 Bed 1 Bath home in Baltimore City!

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 ¥31,577
¥61,972 total
includes taxes & fees
Jun 7 - Jun 8
Bayside Cottage steps from Rock Hall Harbor

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 ¥33,258
¥79,987 total
includes taxes & fees
May 10 - May 11
Charming Pet-Friendly Stay - Near Bay & Beaches.

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 ¥24,855
¥32,255 total
includes taxes & fees
May 20 - May 21
Secluded Tiny Pool House -Private Pool -Self Check in

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 ¥44,635
¥131,075 total
includes taxes & fees
May 10 - May 11
Historic Row Home | Hot Tub - 1 Block from Gate 1!

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 ¥11,356
¥38,438 total
includes taxes & fees
May 25 - May 26
Hidden Fells Point Gem / Private Courtyard Patio

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 ¥44,714
¥87,354 total
includes taxes & fees
May 14 - May 15
5-bedroom vacation home 5 minutes from historic Charlestown

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

Glen Burnie Hideaway - Pet friendly with easy access to multiple attractions.
Glen Burnie
10.0 out of 10, Exceptional, (9 reviews)
"Great experience. "
United States
Shana F.
The price is ¥39,080
¥50,254 total
includes taxes & fees
May 14 - May 15
Glen Burnie Hideaway - Pet friendly with easy access to multiple attractions.

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (53 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is ¥28,390
¥43,468 total
includes taxes & fees
May 13 - May 14
BAYSIDE BUNGALOW

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
Annapolis Home | Fenced Yard | Pool Table | 10 Guests

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 ¥46,896
¥60,411 total
includes taxes & fees
May 8 - May 9
Glen Burnie Escape - Pet friendly with easy access to multiple attractions.

Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (77 reviews)
"Parking availability and restaurant location"
United States
Sophie P.
The price is ¥34,698
¥69,043 total
includes taxes & fees
May 26 - May 27
Cozy 2br home w/ parking in downtown Annapolis

Upscale Escape with Private Garden-Perfect for Relax & Intimate Moments

Upscale Escape with Private Garden-Perfect for Relax & Intimate Moments
Marley
10.0 out of 10, Exceptional, (5 reviews)
The price is ¥56,135
¥113,001 total
includes taxes & fees
May 31 - Jun 1
Upscale Escape with Private Garden-Perfect for Relax & Intimate Moments

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 ¥25,011
¥44,776 total
includes taxes & fees
May 25 - May 26
Family-friendly home in Baltimore with WiFi, AC, Pool table, Washer & dryer
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

Find out more about Chestertown

Chestertown Vacation Homes information

Number of reviews
633
Accommodation
488 Vacation Homes
Lowest Price
¥14,499
Highest Price
¥131,075