Top Vacation Rentals in Chesapeake Bay ᐅ Instant booking

Sun, Mar 28 ±3 - Sun, Mar 28 ±3

We found 892 accommodations in

USA

Maryland

Chesapeake Bay

Vacation apartment for 7 people, with balcony - 1

Park Place - Comfy Condo Close to Beach

300 yd to city/town center

Sleeps 7 pers.3 bedrooms1,798 ft²

BalconyParkingInternet

FREE cancellation

Studio for 8 people, with yard and balcony, kid friendly - 1

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

2.6 mi to city/town center

Sleeps 8 pers.3 bedrooms13,455 ft²

BalconyYardParkingKitchen

FREE cancellation

Secure dataPowered by HoliduReliable service

Cottage for 4 people, with yard - 1

Waterfront Cottage On Candy Point: Family-Friendly and Dog-Friendly!

4.2 mi to city/town center

Sleeps 4 pers.2 bedrooms

YardTerraceParkingInternet

FREE cancellation

Vacation house for 14 people, with terrace - 1

Waterfront Paradise on the Eastern Shore of Chesapeake Bay

2.8 mi to city/town center

Sleeps 14 pers.6 bedrooms4,596 ft²

PoolTerraceParkingInternet

FREE cancellation

Vacation house for 100 people, with terrace and yard - 1

Spacious Home < 1 Mi to Kiptopeke State Park!

450 yd to city/town center

Sleeps 100 pers.4 bedrooms2,562 ft²

YardTerraceParkingInternet

Vacation house for 4 people, with yard and terrace - 1

The Blue Crab Beach House - Free beach passes 🦀

80 yd to city/town center

Sleeps 4 pers.2 bedrooms797 ft²

YardTerraceParkingInternet

FREE cancellation

Vacation house for 4 people, with terrace and yard - 1

Heart of Irvington w/Fireplace Walk to Tides Inn & restaurants - Dog friendly!

650 yd to city/town center

Sleeps 4 pers.2 bedrooms1,292 ft²

YardTerraceParkingInternet

FREE cancellation

Vacation house for 6 people, with yard and terrace, with pets - 1

Sweet Bamboo Beach Cottage

80 yd to city/town center

Sleeps 6 pers.3 bedrooms958 ft²

YardTerraceParkingInternet

FREE cancellation

Vacation house for 6 people, with yard, with pets - 1

Waterfront Getaway with Dock

350 yd to city/town center

Sleeps 6 pers.3 bedrooms

YardParkingInternet

FREE cancellation

Vacation house for 17 people, with lake view and yard - 1

Waterfront Home with pool dock gameroom and kayaks

4.4 mi to city/town center

Sleeps 17 pers.6 bedrooms

BalconyYardTerraceParking

FREE cancellation

Vacation house for 7 people, with yard - 1

Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

1.4 mi to city/town center

Sleeps 7 pers.4 bedrooms

YardTerraceParkingInternet

FREE cancellation

Vacation house for 6 people, with terrace - 1

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

0.6 mi to city/town center

Sleeps 6 pers.3 bedrooms2,099 ft²

TerraceParkingInternet

FREE cancellation

Vacation house for 6 people, with terrace - 1

American Four-Square completely renovated, easy walk to the beach!

500 yd to city/town center

Sleeps 6 pers.3 bedrooms1,798 ft²

TerraceParkingInternet

FREE cancellation

Vacation apartment for 3 people, with balcony - 1

Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!

0.9 mi to city/town center

Sleeps 3 pers.1 bedroom484 ft²

BalconyParkingInternet

FREE cancellation

Vacation house for 3 people, with terrace and yard - 1

Eastport Cottage .5 mi from Downtown Annapolis

0.6 mi to city/town center

Sleeps 3 pers.2 bedrooms

YardTerraceParkingInternet

FREE cancellation

Vacation house for 6 people, with yard and terrace - 1

Charming garden row home, easy 4 block walk to the heart of Annapolis.

450 yd to city/town center

Sleeps 6 pers.3 bedrooms

YardTerraceInternet

FREE cancellation

Vacation house for 6 people, with yard - 1

Waterfront Property, kayaks, private dock, near town

2 mi to city/town center

Sleeps 6 pers.3 bedrooms2,992 ft²

BalconyYardParkingInternet

FREE cancellation

Vacation house for 6 people, with terrace and yard, with pets - 1

Cheerful 3-bedroom waterfront home

1.5 mi to city/town center

Sleeps 6 pers.3 bedrooms1,496 ft²

YardTerraceParkingInternet

FREE cancellation

Vacation house for 3 people, with yard, with pets - 1

Cozy home w/fenced in yard-Dog Friendly with Pet fee. 2 block walk to downtown!

250 yd to city/town center

Sleeps 3 pers.2 bedrooms1,098 ft²

YardTerraceParkingInternet

FREE cancellation

Vacation house for 6 people, with terrace and yard - 1

Sophisticated Charmer with Parking & Views of the Usna Chapel Dome

400 yd to city/town center

Sleeps 6 pers.3 bedrooms1,798 ft²

YardTerraceParkingInternet

FREE cancellation

Cottage for 4 people, with yard, with pets - 1

Summertime where the livin’ is easy at the Rivah in Irvington!

0.7 mi to city/town center

Sleeps 4 pers.2 bedrooms1,690 ft²

YardTerraceParkingInternet

FREE cancellation

Vacation house for 6 people, with yard - 1

Next to the park and 2 blocks to the Beach and restaurants! Right side of Duplex

350 yd to city/town center

Sleeps 6 pers.3 bedrooms

YardTerraceParkingInternet

FREE cancellation

Cottage for 5 people, with hot tub and yard, with pets - 1

Firefly Cottage at the Cape, Hot Tub, Community beach enjoy summer Usna visits.

850 yd to city/town center

Sleeps 5 pers.1 bedroom646 ft²

Hot tubYardTerraceParking

FREE cancellation

Vacation apartment for 6 people, with yard and terrace - 1

Annapolis Condominium in the heart of the historic center

100 yd to city/town center

Sleeps 6 pers.3 bedrooms1,399 ft²

YardTerraceInternet

FREE cancellation

Vacation house for 6 people, with terrace - 1

Bay view from Calvert Cliffs, Solomons Island & State Park nearby

2.8 mi to city/town center

Sleeps 6 pers.3 bedrooms1,399 ft²

TerraceParkingInternet

FREE cancellation

Cottage for 6 people, with yard and terrace - 1

The Yellow Cottage on Harness Creek

1 mi to city/town center

Sleeps 6 pers.2 bedrooms947 ft²

YardTerraceParkingInternet

FREE cancellation

Vacation house for 6 people, with terrace and yard - 1

Stay in the landmark Lighthouse!

200 yd to city/town center

Sleeps 6 pers.3 bedrooms2,293 ft²

YardTerraceParkingInternet

FREE cancellation

Vacation house for 2 people, with terrace, with pets - 1

Blocks to the Boardwalk!

250 yd to city/town center

Sleeps 2 pers.1 bedroom441 ft²

TerraceParkingInternet

FREE cancellation

Vacation house for 4 people, with terrace and yard - 1

Classic Chesapeake Beachside Cottage w/ Porch!

2.2 mi to city/town center

Sleeps 4 pers.2 bedrooms1,313 ft²

YardTerraceParkingInternet

Vacation house for 6 people, with terrace and yard - 1

Sweet Victorian Beach Cottage

800 yd to city/town center

Sleeps 6 pers.3 bedrooms1,690 ft²

YardTerraceParkingInternet

FREE cancellation

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