Top Holiday Rentals in Chesapeake Bay ᐅ Instant booking

Hornsby House Inn

King Suite

550 m to the beach

Sleeps 4 pers.1 bedroom23 m²

GardenTerraceParkingKitchen

6 more units available

Holiday apartment 14m²

11.2 km to the beach

Sleeps 2 pers.1 bedroom14 m²

Hot tubBalconyParkingInternet

3 more units available

Walk to Dtwn: Waterfront Eastern Shore Townhome!

Holiday Home

Sleeps 8 pers.4 bedrooms185 m²

ParkingKitchenInternet

Carpenter Alley Cottage

Three-Bedroom Home

Sleeps 6 pers.4 bedrooms118 m²

GardenParkingKitchenInternet

Charming Havre de Grace Home Walk to Downtown

Three-Bedroom House

10.9 km to the beach

Sleeps 5 pers.3 bedrooms133 m²

TerraceParkingKitchenInternet

The Beach Peach - Downtown location with new charm!

8.9 km to the beach

Sleeps 6 pers.2 bedrooms

ParkingKitchenInternet

Weems Creek Cottage, Annapolis Waterfront

Studio with Sea View

2.8 km to the beach

Sleeps 4 pers.1 bedroom65 m²

ParkingKitchenInternet

Waterfront Paradise w/ Deck ~ 1/2 Mi to Beach

Holiday Home

7.9 km to the beach

Sleeps 8 pers.4 bedrooms241 m²

BalconyParkingKitchenInternet

Southern Breezes Nor' Easter - close to the beach!

8.8 km to the beach

Sleeps 9 pers.3 bedrooms

ParkingKitchenInternet

Historic Inns of Annapolis

Maryland 1 Double Bed

1.7 km to the beach

Sleeps 2 pers.1 bedroom13 m²

TerraceParkingInternet

9 more units available

Vintage Charm: Annapolis Retreat

2.6 km to the beach

Sleeps 4 pers.3 bedrooms204 m²

GardenTerraceParkingKitchen

Sun Outdoors Cape Charles

Two-Bedroom House

6.5 km to the beach

Sleeps 6 pers.2 bedrooms399 m²

PoolTerraceParkingInternet

Maison des Reves - Historic charm in the heart of Downtown!

Four-Bedroom House

8.7 km to the beach

Sleeps 8 pers.4 bedrooms

TerraceParkingKitchenInternet

Pride and Joy of Oxford

Sleeps 6 pers.3 bedrooms163 m²

GardenParkingKitchenInternet

Down By The Docks

Sleeps 6 pers.3 bedrooms

ParkingKitchenInternet

The Dune Beach House

Three-Bedroom House

7.4 km to the beach

Sleeps 6 pers.3 bedrooms111 m²

TerraceKitchenInternet

Near Waterfront, Maryland Renovated Home - Walk to Historic Downtown!

Three-Bedroom House

Sleeps 7 pers.3 bedrooms140 m²

BalconyGardenTerraceParking

Historic Row Home 1 Block from Gate 1 at USNA

Holiday Home

1.6 km to the beach

Sleeps 9 pers.3 bedrooms185 m²

Hot tubGardenTerraceKitchen

Historic Downtown Annapolis Gem Near USNA

Three-Bedroom Townhouse

1.6 km to the beach

Sleeps 6 pers.3 bedrooms111 m²

TerraceParkingKitchenInternet

Waterfront Scotland Beach Retreat w/ Private Beach

Holiday Home

2.4 km to the beach

Sleeps 12 pers.4 bedrooms278 m²

BalconyParkingKitchenInternet

The Wildset

Superior King Room

Sleeps 2 pers.1 bedroom30 m²

GardenParkingInternet

6 more units available

Charming brick home with patio, WiFi, AC, & WD - walk to everything

Holiday Home

1.7 km to the beach

Sleeps 4 pers.2 bedrooms92 m²

Holly Hill Haven

3 km to the beach

Sleeps 10 pers.3 bedrooms137 m²

TerraceParkingKitchenInternet

Riverview Retreat

Three-Bedroom Holiday Home

Sleeps 6 pers.3 bedrooms202 m²

GardenParkingKitchenInternet

❤️Ice Ice Baby❤️Downtown Newport News!

❤️The Safe House❤️Downtown Newport News!

❤️The Speakeasy❤️Downtown Newport News!

The 1850 House

Buckroe Bungalow · #Buckroe Bungalow ~Escape to the Beach 2mins Away!

❤️Breakfast @ Tiffany's❤️Downtown Newport News!

Hornsby House Inn

King Suite

Holiday apartment 14m²

Walk to Dtwn: Waterfront Eastern Shore Townhome!

Holiday Home

Carpenter Alley Cottage

Three-Bedroom Home

Charming Havre de Grace Home Walk to Downtown

Three-Bedroom House

The Beach Peach - Downtown location with new charm!

Weems Creek Cottage, Annapolis Waterfront

Studio with Sea View

Waterfront Paradise w/ Deck ~ 1/2 Mi to Beach

Holiday Home

Southern Breezes Nor' Easter - close to the beach!

Historic Inns of Annapolis

Maryland 1 Double Bed

Vintage Charm: Annapolis Retreat

Sun Outdoors Cape Charles

Two-Bedroom House

Maison des Reves - Historic charm in the heart of Downtown!

Four-Bedroom House

Pride and Joy of Oxford

Down By The Docks

The Dune Beach House

Three-Bedroom House

Near Waterfront, Maryland Renovated Home - Walk to Historic Downtown!

Three-Bedroom House

Historic Row Home 1 Block from Gate 1 at USNA

Holiday Home

Historic Downtown Annapolis Gem Near USNA

Three-Bedroom Townhouse

Waterfront Scotland Beach Retreat w/ Private Beach

Holiday Home

The Wildset

Superior King Room

Charming brick home with patio, WiFi, AC, & WD - walk to everything

Holiday Home

Holly Hill Haven

Riverview Retreat

Three-Bedroom Holiday Home