Search Vacation Homes in Chestertown

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Chestertown vacation 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)
"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 AED 918
AED 1,554 total
includes taxes & fees
1 Apr - 2 Apr
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

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 252
AED 910 total
includes taxes & fees
25 Mar - 26 Mar
Charming Coastal/Country Home w/3 Acres & Sauna!

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 496
AED 1,113 total
includes taxes & fees
25 Mar - 26 Mar
Amazing Modern house with a full kitchen and parking

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, (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 AED 496
AED 1,223 total
includes taxes & fees
29 Mar - 30 Mar
Large 2 bedroom house with private parking in a nice neighborhood

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

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
30 Mar - 31 Mar
Charming 2-bedroom house in Aberdeen with WiFi and AC

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
25 Mar - 26 Mar
Boho Oasis 2 Bed 1 Bath home in Baltimore City!

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 217
AED 738 total
includes taxes & fees
29 Mar - 30 Mar
Hidden Fells Point Gem / Private Courtyard Patio

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 507
AED 1,235 total
includes taxes & fees
30 Mar - 31 Mar
Cozy 2br home w/ parking in downtown Annapolis

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 500
AED 1,189 total
includes taxes & fees
12 Apr - 13 Apr
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

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, (10 reviews)
"Absolutely loved it, very quiet and peaceful, Jordan is an excellent host"
United States
Robert F.
The price is AED 364
AED 498 total
includes taxes & fees
25 Mar - 26 Mar
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, (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 1,925 total
includes taxes & fees
25 Mar - 26 Mar
5-bedroom vacation home 5 minutes from historic Charlestown

Welcome to the secluded waterfront oasis

Welcome to the secluded waterfront oasis
Millington
Welcome to the secluded waterfront oasis

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 757
AED 2,684 total
includes taxes & fees
25 Mar - 26 Mar
Historic Row Home | Hot Tub - 1 Block from Gate 1!

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
25 Mar - 26 Mar
Cozy Private Family Palace near BWI, Pet-Friendly

Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC

Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
Aberdeen
The price is AED 297
AED 645 total
includes taxes & fees
25 Mar - 26 Mar
Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC

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
25 Mar - 26 Mar
Glen Burnie Escape - Pet friendly with easy access to multiple attractions.

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
6 Apr - 7 Apr
Charming Pet-Friendly Stay - Near Bay & Beaches.

Luxury Waterfront Home Built for Entertaining!

Luxury Waterfront Home Built for Entertaining!
Abingdon
9.0 out of 10, Wonderful, (9 reviews)
"Gorgeous waterfront property with easy access to commerce and Baltimore proper. Spacious for large family gatherings, pet-friendly and cozy and warm during winter weather. "
United States
Aaron S.
The price is AED 2,938
AED 4,446 total
includes taxes & fees
25 Mar - 26 Mar
Luxury Waterfront Home Built for Entertaining!

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
27 Mar - 28 Mar
Glen Burnie Hideaway - Pet friendly with easy access to multiple attractions.
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chestertown Hotel Reviews

Explore a world of travel with Expedia