We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday villas in Chestertown, MD

Use a credit card to book with our Peace of Mind Protection.
Learn more
Find a rental
Price per night
Min
to
Max
Bedrooms
Any
Amenities
Select
More filters
Find more rentals you can book on TripAdvisor!   We're showing you properties you can book on TripAdvisor first.
All 51 Rentals in the Chestertown Area
loading...
From
€109
Per Night
Chestertown
3 Bedrooms, 1 Bathroom, Sleeps 7
Bookings
11 photos Details
Reviews (1) Make Enquiry
From
€94
Per Night
Chestertown
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
28 photos Details
Reviews (2) Make Enquiry
From
€230
Per Night
Chestertown
3 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
12 photos Details
Make Enquiry
From
€202
Per Night
Chestertown
1 Bedroom, 1 Bathroom, Sleeps 2
9 photos Details
Make Enquiry

The following rentals are within 40 kilometers of Chestertown, Maryland.

From
€195
Per Night
Rock Hall
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
15 photos Details
Reviews (2) Make Enquiry
From
€312
Per Night
Annapolis
4 Bedrooms, 3 Bathrooms, Sleeps 9
Bookings
30 photos Details
Reviews (2) Make Enquiry
From
€624
Per Night
Annapolis
3 Bedrooms, 3 Bathrooms, Sleeps 10
31 photos Details
Reviews (1) Make Enquiry
From
€195
Per Night
Annapolis
3 Bedrooms, 2 Bathrooms, Sleeps 6
9 photos Details
Reviews (1) Make Enquiry
Get the List
From
€585
Per Night
Annapolis
6 Bedrooms, 5 Bathrooms, Sleeps 12
Bookings
26 photos Details
Reviews (1) Make Enquiry
From
€214
Per Night
Baltimore
2 Bedrooms, 3 Bathrooms, Sleeps 6
Bookings
53 photos Details
Reviews (3) Make Enquiry
From
€195
Per Night
Rock Hall
3 Bedrooms, 2 Bathrooms, Sleeps 7
17 photos Details
Reviews (3) Make Enquiry
From
€94
Per Night
Baltimore
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
7 photos Details
Reviews (4) Make Enquiry
From
€132
Per Night
Annapolis
3 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
4 photos Details
Reviews (2) Make Enquiry
From
€295
Per Night
Baltimore
5 Bedrooms, 6 Bathrooms, Sleeps 8
Bookings
21 photos Details
Reviews (1) Make Enquiry
From
€156
Per Night
Baltimore
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
23 photos Details
Reviews (1) Make Enquiry
From
€156
Per Night
Baltimore
3 Bedrooms, 1 Bathroom, Sleeps 8
Bookings
18 photos Details
Reviews (1) Make Enquiry
From
€156
Per Night
Baltimore
5 Bedrooms, 5 Bathrooms, Sleeps 6
Bookings
7 photos Details
Reviews (3) Make Enquiry
From
€117
Per Night
Baltimore
3 Bedrooms, 1 Bathroom, Sleeps 5
Bookings
19 photos Details
Reviews (6) Make Enquiry
From
€195
Per Night
Baltimore
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
11 photos Details
Reviews (1) Make Enquiry
From
€140
Per Night
Rock Hall
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
12 photos Details
Make Enquiry
From
€136
Per Night
Rock Hall
3 Bedrooms, 3 Bathrooms, Sleeps 9
10 photos Details
Make Enquiry
From
€312
Per Night
Annapolis
2 Bedrooms, 2 Bathrooms, Sleeps 10
23 photos Details
Make Enquiry
From
€136
Per Night
Annapolis
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
14 photos Details
Make Enquiry
From
€79
Per Night
Annapolis
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
7 photos Details
Make Enquiry
From
€90
Per Night
Galena
2 Bedrooms, 1 Bathroom, Sleeps 5
5 photos Details
Make Enquiry
From
€253
Per Night
Baltimore
3 Bedrooms, 2 Bathrooms, Sleeps 9
22 photos Details
Make Enquiry
From
€90
Per Night
Baltimore
2 Bedrooms, 1 Bathroom, Sleeps 4
6 photos Details
Make Enquiry
From
€546
Per Night
Annapolis
5 Bedrooms, 6 Bathrooms, Sleeps 12
Booking
6 photos Details
Make Enquiry
From
€542
Per Night
Annapolis
5 Bedrooms, 3 Bathrooms, Sleeps 20
25 photos Details
Make Enquiry
From
€218
Per Night
Annapolis
4 Bedrooms, 4 Bathrooms, Sleeps 8
3 photos Details
Make Enquiry
From
€1,169
Per Night
Annapolis
4 Bedrooms, 4 Bathrooms, Sleeps 10
Bookings
15 photos Details
Make Enquiry
From
€374
Per Night
Baltimore
3 Bedrooms, 3 Bathrooms, Sleeps 6
8 photos Details
Make Enquiry
From
€94
Per Night
Baltimore
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
4 photos Details
Make Enquiry
From
€195
Per Night
Annapolis
3 Bedrooms, 1 Bathroom, Sleeps 7
20 photos Details
Make Enquiry
From
€117
Per Night
Annapolis
4 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
18 photos Details
Make Enquiry
From
€390
Per Night
Annapolis
1 Bedroom, 2 Bathrooms, Sleeps 4
11 photos Details
Make Enquiry
From
€234
Per Night
Annapolis
1 Bedroom, 1 Bathroom, Sleeps 2
9 photos Details
Make Enquiry
From
€175
Per Night
Baltimore
2 Bedrooms, 1 Bathroom, Sleeps 6
13 photos Details
Reviews (3) Make Enquiry
From
€136
Per Night
Baltimore
1 Bedroom, 1 Bathroom, Sleeps 5
17 photos Details
Reviews (4) Make Enquiry
From
€140
Per Night
Chester
4 Bedrooms, 2 Bathrooms, Sleeps 8
21 photos Details
Reviews (2) Make Enquiry
From
€133
Per Night
Baltimore
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
28 photos Details
Reviews (24) Make Enquiry
From
€156
Per Night
Baltimore
2 Bedrooms, 1 Bathroom, Sleeps 6
14 photos Details
Reviews (3) Make Enquiry
From
€117
Per Night
Baltimore
2 Bedrooms, 1 Bathroom, Sleeps 4
15 photos Details
Reviews (3) Make Enquiry
From
€624
Per Night
Annapolis
4 Bedrooms, 3 Bathrooms, Sleeps 20
20 photos Details
Make Enquiry
From
€253
Per Night
Baltimore
3 Bedrooms, 2 Bathrooms, Sleeps 8
5 photos Details
Make Enquiry
From
€351
Per Night
Grasonville
4 Bedrooms, 3 Bathrooms, Sleeps 10
12 photos Details
Make Enquiry
From
€292
Per Night
Chester
4 Bedrooms, 4 Bathrooms, Sleeps 10
37 photos Details
Make Enquiry
From
€468
Per Night
Annapolis
3 Bedrooms, 4 Bathrooms, Sleeps 10
5 photos Details
Make Enquiry
Go to map view
Book Online(44)
Use filters to find the best results!

Suitability

  • Wheelchair access (5)
  • Elder access (18)
  • Suitable for children (27)
  • Pet friendly (16)
  • Smoking allowed (0)

Amenities

  • Air Conditioning (36)
  • Internet (35)
  • Other outdoor space (31)
  • Washer/Dryer (27)
  • Grill (26)
  • View all amenities
List your property for free!
List your accommodation
for free on our website.
Reach millions worldwide.
Add a Listing


In partnership with
Get the List
Nearby cities