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Our top choices for Chesapeake Beach holiday rentals

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 €359
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 €258
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 €282
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 €406
includes taxes & fees
2 Dec - 3 Dec

5. Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to AnnapolisDeale
8.0 out of 10, Very good, (13 reviews)
The price is €293
includes taxes & fees
15 Nov - 16 Nov

6. 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 €396
includes taxes & fees
13 Nov - 14 Nov

7. 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 €375
includes taxes & fees
1 Dec - 2 Dec

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
9.0 out of 10, Wonderful, (2 reviews)
The price is €321
includes taxes & fees
9 Nov - 10 Nov

9. Plum Point Cottage #17
Plum Point Cottage #17Huntingtown
The price is €412
includes taxes & fees
9 Nov - 10 Nov

10. 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 €352
includes taxes & fees
20 Nov - 21 Nov

11. Plum Point Cottage #14
Plum Point Cottage #14Huntingtown
9.8 out of 10, Exceptional, (10 reviews)
The price is €475
includes taxes & fees
9 Nov - 10 Nov

12. Plum Point Cottage #15
Plum Point Cottage #15Maryland
The price is €508
includes taxes & fees
9 Nov - 10 Nov

13. Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.Benedict
9.0 out of 10, Wonderful, (16 reviews)
The price is €246
includes taxes & fees
10 Nov - 11 Nov

14. 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 €300
includes taxes & fees
23 Nov - 24 Nov

15. 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 €470
includes taxes & fees
9 Nov - 10 Nov

16. 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 €253
includes taxes & fees
16 Nov - 17 Nov

17. 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 €626
includes taxes & fees
11 Nov - 12 Nov

18. Bright and airy waterfront getaway
Bright and airy waterfront getawayBenedict
9.8 out of 10, Exceptional, (26 reviews)
The price is €321
includes taxes & fees
10 Nov - 11 Nov

19. 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 €416
includes taxes & fees
9 Nov - 10 Nov

20. 2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.
2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.Cambridge
The price is €235
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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