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Check prices for these dates

In two weeks
27 Mar - 29 Mar
In two months
8 May - 10 May
In three months
5 Jun - 7 Jun
In four months
3 Jul - 5 Jul

Our top choices for Chestertown holiday homes

Dining

Holiday 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. "
United States
Joe C.
The price is HK$1,955
HK$3,291 total
includes taxes & fees
18 Mar - 19 Mar
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Exterior

Holiday 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."
United States
Brandon D.
The price is HK$554
HK$1,963 total
includes taxes & fees
12 Mar - 13 Mar
Charming Coastal/Country Home w/3 Acres & Sauna!
Interior

Holiday Home in Arnold

Large 2 bedroom house with private parking in a nice neighborhood
9.4 out of 10, Exceptional, (36 reviews)
"Super clean place, great communication from the host, and home is exactly as described and shown in pictures. "
United States
Traci L.
The price is HK$985
HK$2,478 total
includes taxes & fees
15 Mar - 16 Mar
Large 2 bedroom house with private parking in a nice neighborhood
Exterior

Holiday 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 "
United States
Stephanie S.
The price is HK$674
HK$2,107 total
includes taxes & fees
16 Mar - 17 Mar
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Terrace/patio

Holiday Home in Smyrna

Amazing Modern house with a full kitchen and parking
9.2 out of 10, Wonderful, (9 reviews)
"The house is a beautiful place to stay. The location was ideal for going to attractions and stores. "
United States
Laurie S.
The price is HK$929
HK$2,222 total
includes taxes & fees
16 Mar - 17 Mar
Amazing Modern house with a full kitchen and parking
Interior

Holiday Home in Fells Point

Hidden Fells Point Gem / Private Courtyard Patio
9.6 out of 10, Exceptional, (94 reviews)
"Awesome place, great location"
United States
Mark M.
The price is HK$461
HK$1,572 total
includes taxes & fees
15 Mar - 16 Mar
Hidden Fells Point Gem / Private Courtyard Patio
Smart TV, printers

Holiday Home in Berea

Boho Oasis 2 Bed 1 Bath home in Baltimore City!
10.0 out of 10, Exceptional, (4 reviews)
"House kept very clean and neighborhood was really quiet at night! Will be staying again."
United States
Pai’Syn
The price is HK$807
HK$2,071 total
includes taxes & fees
12 Mar - 13 Mar
Boho Oasis 2 Bed 1 Bath home in Baltimore City!
TV

Holiday Home in Aberdeen

Charming 2-bedroom house in Aberdeen with WiFi and AC
7.6 out of 10, Good, (13 reviews)
"Met our needs. Great stay."
United States
Robert C.
The price is HK$528
HK$725 total
includes taxes & fees
15 Mar - 16 Mar
Charming 2-bedroom house in Aberdeen with WiFi and AC
Property grounds

Holiday Home in Perryville

5-bedroom vacation home 5 minutes from historic Charlestown
9.8 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"
United States
Mary D.
The price is HK$2,020
HK$4,097 total
includes taxes & fees
17 Mar - 18 Mar
5-bedroom vacation home 5 minutes from historic Charlestown
Interior

Holiday Home in Historic District

Historic Row Home | Hot Tub - 1 Block from Gate 1!
10.0 out of 10, Exceptional, (5 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 HK$1,166
HK$5,690 total
includes taxes & fees
17 Mar - 18 Mar
Historic Row Home | Hot Tub - 1 Block from Gate 1!
Marina

Holiday Home in Historic District

Cozy 2br home w/ parking in downtown Annapolis
10.0 out of 10, Exceptional, (75 reviews)
"Welcoming host, great location and easy parking "
United States
Chris B.
The price is HK$1,064
HK$2,595 total
includes taxes & fees
30 Mar - 31 Mar
Cozy 2br home w/ parking in downtown Annapolis
Exterior

Holiday Home in Rock Hall

Bayside Cottage steps from Rock Hall Harbor
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 HK$1,369
HK$2,794 total
includes taxes & fees
1 Apr - 2 Apr
Bayside Cottage steps from Rock Hall Harbor
3 bedrooms, iron/ironing board, free WiFi, bed sheets

Holiday Home in Glen Burnie

Glen Burnie Hideaway - Pet friendly with easy access to multiple attractions.
10.0 out of 10, Exceptional, (7 reviews)
"Great experience. "
United States
Shana F.
The price is HK$1,955
HK$2,532 total
includes taxes & fees
23 Mar - 24 Mar
Glen Burnie Hideaway - Pet friendly with easy access to multiple attractions.
Interior

Holiday Home in Glen Burnie

Glen Burnie Escape - Pet friendly with easy access to multiple attractions.
10.0 out of 10, Exceptional, (23 reviews)
"We enjoyed this property so much that we stayed here again just 4 months later."
United States
Kim C.
The price is HK$2,346
HK$3,013 total
includes taxes & fees
15 Mar - 16 Mar
Glen Burnie Escape - Pet friendly with easy access to multiple attractions.
Terrace/patio

Holiday Home in Glen Burnie

Cozy Private Family Palace near BWI, Pet-Friendly
9.8 out of 10, Exceptional, (23 reviews)
"Nice place and good location "
United States
FRANKLIN S.
The price is HK$1,423
HK$3,432 total
includes taxes & fees
16 Mar - 17 Mar
Cozy Private Family Palace near BWI, Pet-Friendly
Property grounds

Holiday Home in Aberdeen

Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
The price is HK$631
HK$1,747 total
includes taxes & fees
13 Mar - 14 Mar
Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
Exterior detail

Holiday Home in Church Hill

Stillwater at Kennersley
The price is HK$3,325
HK$7,953 total
includes taxes & fees
25 Mar - 26 Mar
Stillwater at Kennersley
Interior

Holiday Home in Abingdon

Abingdon Haven Hideaway
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 HK$915
HK$3,009 total
includes taxes & fees
12 Mar - 13 Mar
Abingdon Haven Hideaway
Fridge, microwave, oven, stovetop

Holiday Home in Cape Saint Claire

Neptune by the Water - Pet Friendly Fenced Yard
9.8 out of 10, Exceptional, (11 reviews)
"Enjoyed our stay- thank you!"
United States
KateriK
The price is HK$1,620
HK$4,995 total
includes taxes & fees
6 Apr - 7 Apr
Neptune by the Water - Pet Friendly Fenced Yard
Smart TV

Holiday Home in Berea

Family-friendly home in Baltimore with WiFi, AC, Pool table, Washer & dryer
9.6 out of 10, Exceptional, (5 reviews)
"Amazing house"
United States
Janell W.
The price is HK$789
HK$1,634 total
includes taxes & fees
22 Mar - 23 Mar
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

Pendry Baltimore

Pendry Baltimore

10/10 Excellent
"One of best hotels I’ve stayed in. Staff, the rooms, and hotel bars are top notch! "
Jasmine 3-night trip
Posted 13 hours ago
Pendry Baltimore

Find out more about Chestertown

Chestertown Vacation Homes information

Number of reviews
487
Accommodation
486 Vacation Homes
Lowest Price
HK$725
Highest Price
HK$5,690

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