Top Holiday Rentals in Chesapeake Bay ᐅ Instant booking

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

Historic Beach Front Home: Victorian Elegance. Large Rooms with Amazing bay view

8.8 km to the beach

Sleeps 12 pers.5 bedrooms292 m²

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Tastefully decorated fully-equipped Eastport Annapolis house with water views

1.4 km to the beach

Sleeps 6 pers.3 bedrooms176 m²

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Luxurious waterfront home - Cèilidh

Sleeps 7 pers.4 bedrooms297 m²

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Cozy Beach Bungalow

4.7 km to the beach

Sleeps 6 pers.3 bedrooms92 m²

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Relax or Play on the Choptank River!

Sleeps 2 pers.1 bedroom

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Annapolis Tree House Apartment- luxury shower, separate space

2.5 km to the beach

Sleeps 3 pers.2 bedrooms74 m²

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Annapolis Bayfront Home

1.5 km to the beach

Sleeps 12 pers.5 bedrooms278 m²

Hot tubGardenTerraceParking

Waterfront Condo- Eastport Annapolis- Next to Spa Creek Draw Bridge & Ayc

2 km to the beach

Sleeps 2 pers.2 bedrooms92 m²

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Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay

2.2 km to the beach

Sleeps 6 pers.3 bedrooms92 m²

Hot tubGardenTerraceParking

Enjoys Sunsets on the Creek from our Vintage Cottage tucked away near Bay & Base

4.2 km to the beach

Sleeps 4 pers.3 bedrooms148 m²

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Attractive Waterfront Home over looking Choptank River. Sleeps 5

Sleeps 5 pers.3 bedrooms

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250 Acre Retreat Chesapeake Bay Vacation/Reunion/Wedding 12 Bedrooms, Sleeps 40

9.8 km to the beach

Sleeps 40 pers.12 bedrooms1,045 m²

PoolHot tubBalconyGarden

River House looking at the Chesapeake Bay/Monthly Rental

2.9 km to the beach

Sleeps 8 pers.4 bedrooms

GardenTerraceParkingInternet

Charming Waterfront Escape with beach and pier for fishing and crabbing

650 m to the beach

Sleeps 12 pers.4 bedrooms

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Luxury Beachfront Home on Soft White Sand Beach

11.2 km to the beach

Sleeps 9 pers.5 bedrooms195 m²

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

Modern Chesapeake Waterfront - Heated Pool - Dock

Upscale home with parking for 4 cars in driveway. Walk to downtown.

Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels

Beach House The Real Thing! Direct Beachfront!

A Vacation Away From It All-Family And Pet Friendly

Bicycles, Beach Toys, Kayaks, Chairs & Umbrella - 6 blocks to Beach!

Creekfront/Kayaks/Float Mat/Paddleboard/Privatedock/10Mindrivetomainstreedville

Grandview- Main House

The B&B of Anchorage - Skipjack

Our Always Dreaming Cottage - The Bay At Your Back Steps

Walk to Beach and Shopping from Vibrant Duplex

The Relax-Inn Deal Island with Kayaks and Canoe

Leatherbury Point Bed and Breakfast

\"Cozy\" Waterfront Cottage with Private Pier

Historic Beach Front Home: Victorian Elegance. Large Rooms with Amazing bay view

Tastefully decorated fully-equipped Eastport Annapolis house with water views

Luxurious waterfront home - Cèilidh

Cozy Beach Bungalow

Relax or Play on the Choptank River!

Annapolis Tree House Apartment- luxury shower, separate space

Annapolis Bayfront Home

Waterfront Condo- Eastport Annapolis- Next to Spa Creek Draw Bridge & Ayc

Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay

Enjoys Sunsets on the Creek from our Vintage Cottage tucked away near Bay & Base

Attractive Waterfront Home over looking Choptank River. Sleeps 5

250 Acre Retreat Chesapeake Bay Vacation/Reunion/Wedding 12 Bedrooms, Sleeps 40

River House looking at the Chesapeake Bay/Monthly Rental

Charming Waterfront Escape with beach and pier for fishing and crabbing

Luxury Beachfront Home on Soft White Sand Beach