Top Holiday Rentals in Chesapeake Bay ᐅ Instant booking

Studio for 8 people, with balcony and garden, child-friendly - 1

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

4.2 km to city/town center

Sleeps 8 pers.3 bedrooms1,250 m²

BalconyGardenParkingKitchen

Walk to Dtwn: Waterfront Eastern Shore Townhome!

Holiday Home

700 m to city/town center

Sleeps 8 pers.4 bedrooms185 m²

ParkingKitchenInternet

Carpenter Alley Cottage

Three-Bedroom Home

100 m to city/town center

Sleeps 6 pers.4 bedrooms118 m²

GardenParkingKitchenInternet

Charming Havre de Grace Home Walk to Downtown

Three-Bedroom House

700 m to city/town center

Sleeps 5 pers.3 bedrooms133 m²

TerraceParkingKitchenInternet

The Beach Peach - Downtown location with new charm!

150 m to city/town center

Sleeps 6 pers.2 bedrooms

ParkingKitchenInternet

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

Holiday Home

1.6 km to city/town center

Sleeps 8 pers.4 bedrooms241 m²

BalconyParkingKitchenInternet

Southern Breezes Nor' Easter - close to the beach!

350 m to city/town center

Sleeps 9 pers.3 bedrooms

ParkingKitchenInternet

Historic Inns of Annapolis

Maryland 1 Double Bed

250 m to city/town center

Sleeps 2 pers.1 bedroom13 m²

TerraceParkingInternet

9 more units available

Vintage Charm: Annapolis Retreat

800 m to city/town center

Sleeps 4 pers.3 bedrooms204 m²

GardenTerraceParkingKitchen

Sun Outdoors Cape Charles

Two-Bedroom House

2.4 km to city/town center

Sleeps 6 pers.2 bedrooms399 m²

PoolTerraceParkingInternet

Weems Creek Cottage, Annapolis Waterfront

Studio with Sea View

1.9 km to city/town center

Sleeps 4 pers.1 bedroom65 m²

ParkingKitchenInternet

Holiday Inn Express Prince Frederick by Ihg

600 m to city/town center

Sleeps 4 pers.1 bedroom0 m²

PoolParkingInternet

6 more units available

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

The Dune Beach House

Three-Bedroom House

2 km to city/town center

Sleeps 6 pers.3 bedrooms111 m²

TerraceKitchenInternet

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

Three-Bedroom House

1.6 km to city/town center

Sleeps 7 pers.3 bedrooms140 m²

BalconyGardenTerraceParking

Historic Row Home 1 Block from Gate 1 at USNA

Holiday Home

350 m to city/town center

Sleeps 9 pers.3 bedrooms185 m²

Hot tubGardenTerraceKitchen

Historic Downtown Annapolis Gem Near USNA

Three-Bedroom Townhouse

350 m to city/town center

Sleeps 6 pers.3 bedrooms111 m²

TerraceParkingKitchenInternet

Waterfront Scotland Beach Retreat w/ Private Beach

Holiday Home

19.8 km to city/town center

Sleeps 12 pers.4 bedrooms278 m²

BalconyParkingKitchenInternet

The Wildset

Superior King Room

250 m to city/town center

Sleeps 2 pers.1 bedroom30 m²

GardenParkingInternet

6 more units available

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

Holiday Home

200 m to city/town center

Sleeps 4 pers.2 bedrooms92 m²

Holly Hill Haven

1.9 km to city/town center

Sleeps 10 pers.3 bedrooms137 m²

TerraceParkingKitchenInternet

Riverview Retreat

Three-Bedroom Holiday Home

100 m to city/town center

Sleeps 6 pers.3 bedrooms202 m²

GardenParkingKitchenInternet

Historic Downtown Annapolis w Rooftop Deck

Two-Bedroom Townhouse

250 m to city/town center

Sleeps 6 pers.2 bedrooms96 m²

TerraceParkingKitchenInternet

St Michaels Harbour Inn, Marina and Spa

Double Room

20 m to city/town center

Sleeps 2 pers.1 bedroom0 m²

PoolSaunaTerraceParking

9 more units available

Walk to Everything Historic Arts District

750 m to city/town center

Sleeps 6 pers.2 bedrooms139 m²

BalconyParkingKitchenInternet

Graduate Annapolis

Superior King Room

450 m to city/town center

Sleeps 2 pers.1 bedroom32 m²

TerraceParkingInternet

9 more units available

Rock Hall Retreat w/ Balcony Near Park & Marina!

Holiday Home

150 m to city/town center

Sleeps 6 pers.3 bedrooms145 m²

BalconyParkingKitchenInternet

Cozy Oaks Chesapeake Properties

Holiday Home

600 m to city/town center

Sleeps 6 pers.3 bedrooms89 m²

GardenTerraceParkingKitchen

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

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!

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

Weems Creek Cottage, Annapolis Waterfront

Studio with Sea View

Holiday Inn Express Prince Frederick by Ihg

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

Historic Downtown Annapolis w Rooftop Deck

Two-Bedroom Townhouse

St Michaels Harbour Inn, Marina and Spa

Double Room

Walk to Everything Historic Arts District

Graduate Annapolis

Superior King Room

Rock Hall Retreat w/ Balcony Near Park & Marina!

Holiday Home

Cozy Oaks Chesapeake Properties

Holiday Home