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 Chesapeake Beach, MD

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
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 26 Rentals in the Chesapeake Beach Area
loading...
From
€167
Per Night
Chesapeake Beach
2 Bedrooms, 1 Bathroom, Sleeps 6
12 photos Details
Reviews (2) Make Enquiry
From
€186
Per Night
Chesapeake Beach
4 Bedrooms, 2 Bathrooms, Sleeps 8
27 photos Details
Reviews (3) Make Enquiry

The following rentals are within 30 kilometers of Chesapeake Beach, Maryland.

From
€279
Per Night
St. Michaels
4 Bedrooms, 3 Bathrooms, Sleeps 10
22 photos Details
Reviews (1) Make Enquiry
From
€130
Per Night
Tilghman
3 Bedrooms, 2 Bathrooms, Sleeps 6
20 photos Details
Reviews (2) Make Enquiry
From
€194
Per Night
Saint Leonard
2 Bedrooms, 2 Bathrooms, Sleeps 6
10 photos Details
Make Enquiry
From
€409
Per Night
Oxford
6 Bedrooms, 6 Bathrooms, Sleeps 12
28 photos Details
Make Enquiry
From
€51
Per Night
Davidsonville
2 Bedrooms, 1 Bathroom, Sleeps 4
10 photos Details
Make Enquiry
From
€186
Per Night
Oxford
2 Bedrooms, 2 Bathrooms, Sleeps 6
14 photos Details
Make Enquiry
From
€186
Per Night
Tilghman
1 Bedroom, 1 Bathroom, Sleeps 3
6 photos Details
Make Enquiry
From
€149
Per Night
Davidsonville
2 Bedrooms, 2 Bathrooms, Sleeps 6
8 photos Details
Make Enquiry
Get the List
From
€335
Per Night
St. Michaels
3 Bedrooms, 3 Bathrooms, Sleeps 10
13 photos Details
Make Enquiry
From
€565
Per Night
St. Michaels
6 Bedrooms, 6 Bathrooms, Sleeps 12
38 photos Details
Make Enquiry
From
€261
Per Night
Tilghman
1 Bedroom, 1 Bathroom, Sleeps 4
12 photos Details
Reviews (6) Make Enquiry
From
€134
Per Night
St. Michaels
2 Bedrooms, 2 Bathrooms, Sleeps 5
20 photos Details
Reviews (11) Make Enquiry
From
€495
Per Night
Bozman
4 Bedrooms, 3 Bathrooms, Sleeps 13
7 photos Details
Reviews (8) Make Enquiry
From
€279
Per Night
Bozman
2 Bedrooms, 1 Bathroom, Sleeps 6
9 photos Details
Reviews (1) Make Enquiry
From
€268
Per Night
St. Michaels
7 Bedrooms, 4 Bathrooms, Sleeps 11
12 photos Details
Reviews (1) Make Enquiry
From
€100
Per Night
North Beach
1 Bedroom, 1 Bathroom, Sleeps 5
17 photos Details
Reviews (4) Make Enquiry
From
€223
Per Night
Riva
3 Bedrooms, 3 Bathrooms, Sleeps 6
17 photos Details
Make Enquiry
From
€186
Per Night
Claiborne
3 Bedrooms, 4 Bathrooms, Sleeps 8
11 photos Details
Make Enquiry
From
€893
Per Week
North Beach
4 Bedrooms, 3 Bathrooms, Sleeps 8
27 photos Details
Make Enquiry
From
€186
Per Night
Deale
4 Bedrooms, 3 Bathrooms, Sleeps 10
12 photos Details
Make Enquiry
From
€260
Per Night
North Beach
2 Bedrooms, 2 Bathrooms, Sleeps 5
17 photos Details
Make Enquiry
From
€141
Per Night
St. Michaels
2 Bedrooms, 2 Bathrooms, Sleeps 4
7 photos Details
Make Enquiry
From
€74
Per Night
North Beach
2 Bedrooms, 1 Bathroom, Sleeps 4
9 photos Details
Make Enquiry
From
€2,457
Per Week
North Beach
3 Bedrooms, 2 Bathrooms, Sleeps 7
20 photos Details
Make Enquiry
Go to map view
Book Online(10)
Use filters to find the best results!

Suitability

  • Wheelchair access (3)
  • Elder access (8)
  • Suitable for children (16)
  • Pet friendly (10)
  • Smoking allowed (2)

Amenities

  • Air Conditioning (24)
  • Other outdoor space (22)
  • Grill (21)
  • Internet (19)
  • Parking (19)
  • 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