
Holiday Homes in Chesapeake Beach
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Our top choices for Chesapeake Beach holiday homes

1. Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Beach Front, Bay View, Fishing, chesapeake,Family GetawayChesapeak beach
9.2 out of 10, Wonderful, (7 reviews)
The price is AU$572
includes taxes & fees
2 Dec - 3 Dec

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 AU$434
includes taxes & fees
12 Nov - 13 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 AU$449
includes taxes & fees
9 Nov - 10 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, (40 reviews)
The price is AU$650
includes taxes & fees
2 Dec - 3 Dec

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, (1 review)
The price is AU$627
includes taxes & fees
13 Nov - 14 Nov

6. 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)
The price is AU$570
includes taxes & fees
20 Nov - 21 Nov

7. 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
9.0 out of 10, Wonderful, (2 reviews)
The price is AU$517
includes taxes & fees
9 Nov - 10 Nov

8. 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 AU$606
includes taxes & fees
1 Dec - 2 Dec

9. 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 AU$487
includes taxes & fees
23 Nov - 24 Nov

10. 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 AU$663
includes taxes & fees
9 Nov - 10 Nov

11. Family Home on Mayo Peninsula | Deck | Sleeps 10
Family Home on Mayo Peninsula | Deck | Sleeps 10Edgewater
10.0 out of 10, Exceptional, (6 reviews)
The price is AU$1,025
includes taxes & fees
11 Nov - 12 Nov

12. 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, (8 reviews)
The price is AU$417
includes taxes & fees
16 Nov - 17 Nov

13. Bright and airy waterfront getaway
Bright and airy waterfront getawayBenedict
9.8 out of 10, Exceptional, (26 reviews)
The price is AU$526
includes taxes & fees
10 Nov - 11 Nov

14. 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 AU$769
includes taxes & fees
9 Nov - 10 Nov

15. 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 AU$699
includes taxes & fees
2 Dec - 3 Dec

16. 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 AU$796
includes taxes & fees
29 Nov - 30 Nov

17. Londontowne Home | Beach | 3BR
Londontowne Home | Beach | 3BREdgewater
9.4 out of 10, Exceptional, (3 reviews)
The price is AU$1,036
includes taxes & fees
9 Nov - 10 Nov

18. Tranquil Modern Farmhouse
Tranquil Modern FarmhouseWaldorf
9.2 out of 10, Wonderful, (10 reviews)
The price is AU$1,059
includes taxes & fees
16 Nov - 17 Nov

19. 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)
The price is AU$1,774
includes taxes & fees
1 Dec - 2 Dec

20. The Harness Creek Retreat in Annapolis
The Harness Creek Retreat in AnnapolisHillsmere
The price is AU$598
includes taxes & fees
9 Nov - 10 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.
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Top Chesapeake Beach Hotel Reviews

Courtyard Marriott Waldorf
8/10 Good
Find out more about Chesapeake Beach
Chesapeake Beach Holiday Homes information
Number of reviews | 282 |
|---|---|
Accommodation | 401 Holiday Homes |
Lowest Price | AU$417 |
Highest Price | AU$1,774 |



































































