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Vacation Rentals in Chestertown, MD and nearby

Professionally managed typically means…
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
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All 45 Rentals in the Chestertown Area
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From
$120
Per Night
Chestertown
1 Bedroom, 1 Bathroom, Sleeps 4
20 photos Details
Reviews (2) Make Inquiry
From
$99
Per Night
Chestertown
1 Bedroom, 1 Bathroom, Sleeps 4
7 photos Details
Reviews (4) Make Inquiry
From
$140
Per Night
Chestertown
3 Bedrooms, 1 Bathroom, Sleeps 7
11 photos Details
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From
$295
Per Night
Chestertown
3 Bedrooms, 3 Bathrooms, Sleeps 8
12 photos Details
Make Inquiry
From
$259
Per Night
Chestertown
1 Bedroom, 1 Bathroom, Sleeps 2
9 photos Details
Make Inquiry

The following rentals are within 25 miles of Chestertown, Maryland.

From
$250
Per Night
Rock Hall
3 Bedrooms, 2 Bathrooms, Sleeps 7
17 photos Details
Reviews (3) Make Inquiry
From
$120
Per Night
Baltimore
1 Bedroom, 1 Bathroom, Sleeps 2
7 photos Details
Reviews (3) Make Inquiry
From
$200
Per Night
Baltimore
3 Bedrooms, 2 Bathrooms, Sleeps 8
23 photos Details
Reviews (1) Make Inquiry
From
$399
Per Night
Baltimore
5 Bedrooms, 6 Bathrooms, Sleeps 8
21 photos Details
Reviews (1) Make Inquiry
From
$144
Per Night
Annapolis
3 Bedrooms, 2 Bathrooms, Sleeps 4
4 photos Details
Reviews (2) Make Inquiry
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From
$400
Per Night
Annapolis
4 Bedrooms, 3 Bathrooms, Sleeps 9
30 photos Details
Reviews (2) Make Inquiry
From
$250
Per Night
Baltimore
2 Bedrooms, 1 Bathroom, Sleeps 6
11 photos Details
Reviews (1) Make Inquiry
From
$800
Per Night
Annapolis
3 Bedrooms, 3 Bathrooms, Sleeps 10
31 photos Details
Reviews (1) Make Inquiry
From
$180
Per Night
Chester
4 Bedrooms, 2 Bathrooms, Sleeps 8
21 photos Details
Reviews (2) Make Inquiry
From
$350
Per Night
Baltimore
3 Bedrooms, 3 Bathrooms, Sleeps 6
54 photos Details
Reviews (3) Make Inquiry
From
$200
Per Night
Baltimore
2 Bedrooms, 1 Bathroom, Sleeps 6
14 photos Details
Reviews (3) Make Inquiry
From
$200
Per Night
Baltimore
2 Bedrooms, 1 Bathroom, Sleeps 6
13 photos Details
Reviews (3) Make Inquiry
From
$200
Per Night
Baltimore
3 Bedrooms, 1 Bathroom, Sleeps 8
18 photos Details
Reviews (1) Make Inquiry
From
$150
Per Night
Baltimore
3 Bedrooms, 1 Bathroom, Sleeps 5
19 photos Details
Reviews (5) Make Inquiry
From
$200
Per Night
Baltimore
5 Bedrooms, 5 Bathrooms, Sleeps 6
7 photos Details
Reviews (1) Make Inquiry
From
$170
Per Night
Baltimore
3 Bedrooms, 2 Bathrooms, Sleeps 6
28 photos Details
Reviews (22) Make Inquiry
From
$175
Per Night
Baltimore
1 Bedroom, 1 Bathroom, Sleeps 5
17 photos Details
Reviews (4) Make Inquiry
From
$150
Per Night
Baltimore
2 Bedrooms, 1 Bathroom, Sleeps 4
15 photos Details
Reviews (2) Make Inquiry
From
$180
Per Night
Rock Hall
1 Bedroom, 1 Bathroom, Sleeps 4
12 photos Details
Make Inquiry
From
$175
Per Night
Rock Hall
3 Bedrooms, 3 Bathrooms, Sleeps 9
10 photos Details
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From
$115
Per Night
Galena
2 Bedrooms, 1 Bathroom, Sleeps 5
5 photos Details
Make Inquiry
From
$101
Per Night
Annapolis
3 Bedrooms, 2 Bathrooms, Sleeps 8
7 photos Details
Make Inquiry
From
$120
Per Night
Baltimore
1 Bedroom, 1 Bathroom, Sleeps 2
4 photos Details
Make Inquiry
From
$695
Per Night
Annapolis
5 Bedrooms, 3 Bathrooms, Sleeps 20
25 photos Details
Make Inquiry
From
$250
Per Night
Annapolis
3 Bedrooms, 2 Bathrooms, Sleeps 6
23 photos Details
Make Inquiry
From
$750
Per Night
Annapolis
6 Bedrooms, 5 Bathrooms, Sleeps 12
26 photos Details
Make Inquiry
From
$250
Per Night
Annapolis
3 Bedrooms, 2 Bathrooms, Sleeps 6
9 photos Details
Make Inquiry
From
$350
Per Night
Severna Park
3 Bedrooms, 3 Bathrooms, Sleeps 10
21 photos Details
Make Inquiry
From
$325
Per Night
Baltimore
3 Bedrooms, 2 Bathrooms, Sleeps 9
22 photos Details
Make Inquiry
From
$1,500
Per Night
Annapolis
4 Bedrooms, 4 Bathrooms, Sleeps 10
15 photos Details
Make Inquiry
From
$295
Per Night
Baltimore
3 Bedrooms, 2 Bathrooms, Sleeps 6
5 photos Details
Make Inquiry
From
$900
Per Night
Arnold
4 Bedrooms, 4 Bathrooms, Sleeps 10
14 photos Details
Make Inquiry
From
$175
Per Night
Annapolis
1 Bedroom, 1 Bathroom, Sleeps 4
14 photos Details
Make Inquiry
From
$3,150
Per Month
Annapolis
1 Bedroom, 1 Bathroom, Sleeps 1
5 photos Details
Make Inquiry
From
$700
Per Night
Annapolis
5 Bedrooms, 6 Bathrooms, Sleeps 12
6 photos Details
Make Inquiry
From
$250
Per Night
Annapolis
4 Bedrooms, 4 Bathrooms, Sleeps 8
3 photos Details
Make Inquiry
From
$250
Per Night
Rock Hall
3 Bedrooms, 2 Bathrooms, Sleeps 6
15 photos Details
Make Inquiry
From
$500
Per Night
Annapolis
1 Bedroom, 2 Bathrooms, Sleeps 4
11 photos Details
Make Inquiry
From
$300
Per Night
Annapolis
1 Bedroom, 1 Bathroom, Sleeps 2
9 photos Details
Make Inquiry
From
$150
Per Night
Annapolis
4 Bedrooms, 2 Bathrooms, Sleeps 8
18 photos Details
Make Inquiry
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Book Online(42)
Use filters to find the best results!

Suitability

  • Wheelchair access (5)
  • Elder access (17)
  • Suitable for children (25)
  • Pet friendly (13)
  • Smoking allowed (1)

Amenities

  • Air Conditioning (33)
  • Internet (32)
  • Other outdoor space (28)
  • Washer/Dryer (23)
  • Grill (22)
  • View all amenities
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Book Online(42)

Suitability

  • Wheelchair access (5)
  • Elder access (17)
  • Suitable for children (25)
  • Pet friendly (13)
  • Smoking allowed (1)

Amenities

  • Air Conditioning (33)
  • Internet (32)
  • Other outdoor space (28)
  • Washer/Dryer (23)
  • Grill (22)
  • View all amenities