
Search Vacation Homes in Chesapeake Beach
- Change your mindBook hotels with free cancellation
- Be pickySearch 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 Chesapeake Beach vacation homes

1. Family Beach House: Spacious Deck, Grill & Views
Family Beach House: Spacious Deck, Grill & ViewsChesapeak beach
9.2 out of 10, Wonderful, (7 reviews)

2. Beachside Oasis with Beach Passes & King Suite by A Haven Away
Beachside Oasis with Beach Passes & King Suite by A Haven AwayNorth Beach
10.0 out of 10, Exceptional, (25 reviews)
The price is AED 323
AED 1,137 total
includes taxes & fees
16 Nov - 17 Nov

3. The Cozy Crab- Your Charming Haven in Lovely North Beach!
The Cozy Crab- Your Charming Haven in Lovely North Beach!North Beach
9.6 out of 10, Exceptional, (30 reviews)
The price is AED 533
AED 1,145 total
includes taxes & fees
16 Nov - 17 Nov

4. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, RestaurantsNorth Beach
10.0 out of 10, Exceptional, (41 reviews)
The price is AED 405
AED 1,446 total
includes taxes & fees
16 Nov - 17 Nov

5. 3-bedroom house in Deale located on Bay many amenities and great views
3-bedroom house in Deale located on Bay many amenities and great viewsDeale
10.0 out of 10, Exceptional, (2 reviews)
The price is AED 661
AED 1,604 total
includes taxes & fees
16 Nov - 17 Nov

6. Relax on Kent Island in 4 Bedroom Home w/Waterview
Relax on Kent Island in 4 Bedroom Home w/WaterviewStevensville
9.8 out of 10, Exceptional, (57 reviews)
The price is AED 375
AED 1,128 total
includes taxes & fees
23 Nov - 24 Nov

7. Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.Prince Frederick
9.2 out of 10, Wonderful, (12 reviews)

8. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach AccessShady Side
9.4 out of 10, Exceptional, (3 reviews)
The price is AED 628
AED 1,323 total
includes taxes & fees
14 Dec - 15 Dec

9. Sunset Cottage - West River Access and Views!
Sunset Cottage - West River Access and Views!Shady Side
9.8 out of 10, Exceptional, (6 reviews)
The price is AED 801
AED 1,645 total
includes taxes & fees
15 Dec - 16 Dec

10. Bright and airy waterfront getaway
Bright and airy waterfront getawayBenedict
9.8 out of 10, Exceptional, (26 reviews)
The price is AED 845
AED 1,343 total
includes taxes & fees
16 Nov - 17 Nov

11. Renovated Bungalow | Walk to Beach | Dog-Friendly
Renovated Bungalow | Walk to Beach | Dog-FriendlyEdgewater
9.6 out of 10, Exceptional, (14 reviews)
The price is AED 707
AED 1,958 total
includes taxes & fees
16 Nov - 17 Nov

12. Family Home on Mayo Peninsula | Deck | Sleeps 10
Family Home on Mayo Peninsula | Deck | Sleeps 10Edgewater
9.8 out of 10, Exceptional, (7 reviews)
The price is AED 889
AED 2,471 total
includes taxes & fees
16 Nov - 17 Nov

13. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community BeachArundel on the Bay
9.6 out of 10, Exceptional, (19 reviews)
The price is AED 760
AED 1,734 total
includes taxes & fees
16 Nov - 17 Nov

14. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays
3-bedroom house in soothing Saint Leonard with AC for relaxing staysSaint Leonard
10.0 out of 10, Exceptional, (9 reviews)
The price is AED 522
AED 1,033 total
includes taxes & fees
16 Nov - 17 Nov

15. Annapolis Retreat - 7 mins from downtown Annapolis!
Annapolis Retreat - 7 mins from downtown Annapolis!Hillsmere
10.0 out of 10, Exceptional, (6 reviews)
The price is AED 771
AED 1,951 total
includes taxes & fees
30 Nov - 1 Dec

16. WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8Cambridge
10.0 out of 10, Exceptional, (17 reviews)
The price is AED 935
AED 1,708 total
includes taxes & fees
19 Nov - 20 Nov

17. Londontowne Home | Beach | 3BR
Londontowne Home | Beach | 3BREdgewater
9.4 out of 10, Exceptional, (3 reviews)
The price is AED 889
AED 2,601 total
includes taxes & fees
16 Nov - 17 Nov

18. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!Stevensville
10.0 out of 10, Exceptional, (75 reviews)

19. Londontowne Rancher | 3BR | Near Waterfront
Londontowne Rancher | 3BR | Near WaterfrontEdgewater
7.0 out of 10, Good, (2 reviews)
The price is AED 970
AED 2,450 total
includes taxes & fees
30 Nov - 1 Dec

20. Tranquil Modern Farmhouse
Tranquil Modern FarmhouseWaldorf
9.2 out of 10, Wonderful, (10 reviews)
The price is AED 1,500
AED 2,683 total
includes taxes & fees
16 Nov - 17 Nov
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.
Find vacation rentals that suit your style
Private vacation homes
Apartments
Save an average of 15% on thousands of hotels when you're signed in
Top Chesapeake Beach Hotel Reviews

Spark by Hilton Waldorf
10/10 Excellent



































































