Top Holiday Rentals in Chesapeake Bay ᐅ Instant booking

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

Holiday Inn Express & Suites Annapolis by IHG

Standard Room

650 m to city/town center

Sleeps 2 pers.1 bedroom27 m²

ParkingInternet

9 more units available

Sandaway Suites & Beach

Suite with Bay View

9.1 km to city/town center

Sleeps 2 pers.1 bedroom34 m²

GardenTerraceParkingInternet

3 more units available

Sunny Shores Retreat with Private Pool

7 km to city/town center

Sleeps 8 pers.4 bedrooms

BalconyGardenTerraceParking

The Retro Pad

Three-Bedroom House

4.8 km to city/town center

Sleeps 6 pers.3 bedrooms176 m²

BalconyTerraceParkingKitchen

The Still Pond Inn

One-Bedroom Apartment

400 m to city/town center

Sleeps 2 pers.1 bedroom42 m²

GardenTerraceParkingKitchen

2 more units available

Historic Charm Steps from City Dock and the Yard

Holiday Home

350 m to city/town center

Sleeps 6 pers.2 bedrooms185 m²

GardenTerraceKitchenInternet

DTA Row Home Walk to City Dock & The Yard

Holiday Home

350 m to city/town center

Sleeps 6 pers.2 bedrooms204 m²

TerraceKitchenInternet

Inn at Leonardtown

100 m to city/town center

Sleeps 1 pers.1 bedroom

ParkingInternet

5 more units available

Pint-Sized on Poplar

Apartment

800 m to city/town center

Sleeps 2 pers.1 bedroom

ParkingKitchenInternet

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

KitchenInternet

One more unit available

Renovated 3BR Near Sandy Point Beach

Holiday Home

2 km to city/town center

Sleeps 8 pers.3 bedrooms167 m²

BalconyGardenTerraceParking

Charming Victorian Farmhouse on Historic Main St

Holiday Home

500 m to city/town center

Sleeps 6 pers.3 bedrooms195 m²

TerraceParkingKitchenInternet

Walk to Parks & Marina! Waterfront Cambridge Condo

Apartment

1.7 km to city/town center

Sleeps 6 pers.2 bedrooms74 m²

TerraceParkingKitchenInternet

Walk to the Beach! Beach Passes | Games I King Bed

Holiday Home

50 m to city/town center

Sleeps 6 pers.3 bedrooms104 m²

BalconyGardenTerraceParking

Chesapeake Holiday House

Three-Bedroom House

3.7 km to city/town center

Sleeps 6 pers.3 bedrooms111 m²

GardenTerraceParkingKitchen

Northern Neck Nature Retreat w/ Boat Ramp & Dock!

Holiday Home

3.9 km to city/town center

Sleeps 7 pers.3 bedrooms106 m²

BalconyTerraceParkingKitchen

Pet-Friendly Cottage Walk to USNA Stadium

Holiday Home

1.7 km to city/town center

Sleeps 6 pers.3 bedrooms157 m²

GardenTerraceParkingKitchen

3 Mi to Washington College! Updated Home w/ Patio

Holiday Home

2.1 km to city/town center

Sleeps 6 pers.3 bedrooms92 m²

TerraceParkingKitchenInternet

Walk to DTA & USNA Pet-Friendly Home

Holiday Home

1.3 km to city/town center

Sleeps 6 pers.3 bedrooms185 m²

GardenTerraceParkingKitchen

Annapolis Waterfront Hotel, Autograph Collection

Double Room with 2 Double Beds

300 m to city/town center

Sleeps 4 pers.1 bedroom20 m²

TerraceParkingInternet

9 more units available

Hummingbird Inn

Premium Quadruple Room

13.2 km to city/town center

Sleeps 4 pers.1 bedroom39 m²

Hot tubGardenTerraceParking

5 more units available

Luxury 2-Bedroom House in superb Norfolk With Cool AC and Charm

Two-Bedroom House

4.6 km to city/town center

Sleeps 4 pers.2 bedrooms111 m²

TerraceParkingKitchenInternet

Waterfront Gem < 1 Mi to Dtwn Cambridge!

Apartment

1.8 km to city/town center

Sleeps 4 pers.1 bedroom69 m²

ParkingKitchenInternet

Walk to Historic Chestertown: Dog-Friendly Retreat

Holiday Home

250 m to city/town center

Sleeps 6 pers.2 bedrooms89 m²

ParkingKitchenInternet

Waterfront, Private Beach, & Dock in Irvington

Holiday Home

800 m to city/town center

Sleeps 10 pers.4 bedrooms464 m²

BalconyGardenTerraceParking

Annapolis Charm Waterfront Getaway Near USNA - FISH & CRAB from your PRIVATE PIER!

Three-Bedroom Villa

4 km to city/town center

Sleeps 8 pers.3 bedrooms125 m²

BalconyGardenTerraceParking

The Westin Annapolis

Jr Suite, Junior Suite, 1 King

1.1 km to city/town center

Sleeps 3 pers.1 bedroom48 m²

PoolHot tubParkingInternet

7 more units available

Buckroe Bungalow in Hampton

Flat 207 with Fireplace in Saint Michaels

The Bungalow at Sunny Shores with Pool

Holiday Inn Express & Suites Annapolis by IHG

Standard Room

Sandaway Suites & Beach

Suite with Bay View

Sunny Shores Retreat with Private Pool

The Retro Pad

Three-Bedroom House

The Still Pond Inn

One-Bedroom Apartment

Historic Charm Steps from City Dock and the Yard

Holiday Home

DTA Row Home Walk to City Dock & The Yard

Holiday Home

Inn at Leonardtown

Pint-Sized on Poplar

Apartment

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

Holiday Home

Renovated 3BR Near Sandy Point Beach

Holiday Home

Charming Victorian Farmhouse on Historic Main St

Holiday Home

Walk to Parks & Marina! Waterfront Cambridge Condo

Apartment

Walk to the Beach! Beach Passes | Games I King Bed

Holiday Home

Chesapeake Holiday House

Three-Bedroom House

Northern Neck Nature Retreat w/ Boat Ramp & Dock!

Holiday Home

Pet-Friendly Cottage Walk to USNA Stadium

Holiday Home

3 Mi to Washington College! Updated Home w/ Patio

Holiday Home

Walk to DTA & USNA Pet-Friendly Home

Holiday Home

Annapolis Waterfront Hotel, Autograph Collection

Double Room with 2 Double Beds

Hummingbird Inn

Premium Quadruple Room

Luxury 2-Bedroom House in superb Norfolk With Cool AC and Charm

Two-Bedroom House

Waterfront Gem < 1 Mi to Dtwn Cambridge!

Apartment

Walk to Historic Chestertown: Dog-Friendly Retreat

Holiday Home

Waterfront, Private Beach, & Dock in Irvington

Holiday Home

Annapolis Charm Waterfront Getaway Near USNA - FISH & CRAB from your PRIVATE PIER!

Three-Bedroom Villa

The Westin Annapolis

Jr Suite, Junior Suite, 1 King