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Check prices for these dates

In two weeks
10 Apr - 12 Apr
In two months
22 May - 24 May
In three months
19 Jun - 21 Jun
In four months
17 Jul - 19 Jul

Our top choices for Chestertown vacation homes

Dining

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)
"The owner was very nice and prompt at responding. The house was comfortable. A little short on extras but suited our purpose. (there is not an ice maker, but she has a small ice machine that is not enough for 4 people- just one small example). "
United States
Alison B.
The price is AED 918
AED 1,546 total
includes taxes & fees
30 Mar - 31 Mar
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Interior

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, (37 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 1,223 total
includes taxes & fees
29 Mar - 30 Mar
Large 2 bedroom house with private parking in a nice neighborhood
Terrace/patio

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, (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 AED 433
AED 1,037 total
includes taxes & fees
30 Mar - 31 Mar
Amazing Modern house with a full kitchen and parking
Smart TV, printers

Boho Oasis 2 Bed 1 Bath home in Baltimore City!

Boho Oasis 2 Bed 1 Bath home in Baltimore City!
Berea
9.6 out of 10, Exceptional, (5 reviews)
"House kept very clean and neighborhood was really quiet at night! Will be staying again."
United States
Pai’Syn
The price is AED 379
AED 972 total
includes taxes & fees
29 Mar - 30 Mar
Boho Oasis 2 Bed 1 Bath home in Baltimore City!
Interior

Hidden Fells Point Gem / Private Courtyard Patio

Hidden Fells Point Gem / Private Courtyard Patio
Fells Point
9.6 out of 10, Exceptional, (94 reviews)
"Awesome place, great location"
United States
Mark M.
The price is AED 264
AED 793 total
includes taxes & fees
12 Apr - 13 Apr
Hidden Fells Point Gem / Private Courtyard Patio
TV

Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
7.6 out of 10, Good, (13 reviews)
"Met our needs. Great stay."
United States
Robert C.
The price is AED 248
AED 341 total
includes taxes & fees
7 Apr - 8 Apr
Charming 2-bedroom house in Aberdeen with WiFi and AC
Marina

Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (75 reviews)
"Welcoming host, great location and easy parking "
United States
Chris B.
The price is AED 514
AED 1,244 total
includes taxes & fees
30 Mar - 31 Mar
Cozy 2br home w/ parking in downtown Annapolis
Exterior

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 440
AED 1,129 total
includes taxes & fees
8 Apr - 9 Apr
Charming Coastal/Country Home w/3 Acres & Sauna!
Sun loungers, beach towels

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, (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 AED 949
AED 1,917 total
includes taxes & fees
30 Mar - 31 Mar
5-bedroom vacation home 5 minutes from historic Charlestown
Exterior

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 460
AED 1,142 total
includes taxes & fees
12 Apr - 13 Apr
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Smart TV

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 1,320 total
includes taxes & fees
13 Apr - 14 Apr
Bayside Cottage steps from Rock Hall Harbor
Dining

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 1,968 total
includes taxes & fees
7 Apr - 8 Apr
Charming Pet-Friendly Stay - Near Bay & Beaches.
Terrace/patio

Cozy Private Family Palace near BWI, Pet-Friendly

Cozy Private Family Palace near BWI, Pet-Friendly
Glen Burnie
9.8 out of 10, Exceptional, (23 reviews)
"Nice place and good location "
United States
FRANKLIN S.
The price is AED 793
AED 1,708 total
includes taxes & fees
29 Mar - 30 Mar
Cozy Private Family Palace near BWI, Pet-Friendly
Interior

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, (25 reviews)
"We enjoyed this property so much that we stayed here again just 4 months later."
United States
Kim C.
The price is AED 1,102
AED 1,436 total
includes taxes & fees
30 Mar - 31 Mar
Glen Burnie Escape - Pet friendly with easy access to multiple attractions.
3 bedrooms, iron/ironing board, free WiFi, bed sheets

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, (8 reviews)
"Great experience. "
United States
Shana F.
The price is AED 918
AED 1,198 total
includes taxes & fees
29 Mar - 30 Mar
Glen Burnie Hideaway - Pet friendly with easy access to multiple attractions.
Smart TV

The Hideaway Spot- Waterfront w/ Dock on Long Cove

The Hideaway Spot- Waterfront w/ Dock on Long Cove
Glen Burnie
8.8 out of 10, Excellent, (10 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 418
AED 1,310 total
includes taxes & fees
30 Mar - 31 Mar
The Hideaway Spot- Waterfront w/ Dock on Long Cove
Interior

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

Historic Row Home | Hot Tub - 1 Block from Gate 1!
Historic District
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 AED 907
AED 2,881 total
includes taxes & fees
7 Apr - 8 Apr
Historic Row Home | Hot Tub - 1 Block from Gate 1!
Fridge, microwave, oven, stovetop

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 749
AED 2,332 total
includes taxes & fees
13 Apr - 14 Apr
Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Exterior detail

Pool + Hot Tub + Pickleball | Waterfront

Pool + Hot Tub + Pickleball | Waterfront
Church Hill
The price is AED 1,275
AED 3,346 total
includes taxes & fees
31 Mar - 1 Apr
Pool + Hot Tub + Pickleball | Waterfront
Interior

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 AED 430
AED 1,406 total
includes taxes & fees
28 Mar - 29 Mar
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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Top Chestertown Hotel Reviews

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

6/10 Okay
"So a couple of years back when my wife and I stayed here it was pretty decent. Not sure what has happened as of late, but the elevator doesn't work, the breakfast was less than average and there are prostitutes housed at the location. Had I known, I wouldn't have booked the place. "
Wayne 3-night trip
Posted 1 hour ago
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

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