Top Vacation Rentals in Chesapeake Bay ᐅ Instant booking

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

Mariners Cove Waterfront - Private Dock, Pet Friendly, Wi-Fi, Off-Street Parking

500 yd to city/town center

Sleeps 12 pers.3 bedrooms3,498 ft²

BalconyYardParkingInternet

Romantic Waterfront Abode with Patio & Dock!

10.3 mi to city/town center

Sleeps 2 pers.1 bedroom743 ft²

Balcony/TerraceYardParkingInternet

Sunny Shores Retreat with Private Pool

4.4 mi to city/town center

Sleeps 8 pers.4 bedrooms

BalconyYardTerraceParking

Relaxation awaits! Potomac River Waterfront Home.

4 mi to city/town center

Sleeps 8 pers.3 bedrooms1,733 ft²

YardTerraceParkingInternet

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

Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!

0.9 mi to city/town center

Sleeps 3 pers.1 bedroom484 ft²

BalconyParkingInternet

Clean and Cozy 2 Br home blocks away from downtown

250 yd to city/town center

Sleeps 6 pers.2 bedrooms

Beachfront Getaway, Dolphin Suite, 🐶 💙

1.1 mi to city/town center

Sleeps 6 pers.3 bedrooms2,067 ft²

TerraceParkingInternet

One more unit available

The Blue Crab Beach House - Free beach passes 🦀

80 yd to city/town center

Sleeps 4 pers.2 bedrooms797 ft²

YardTerraceParkingInternet

Cozy Cottage - quaint and comfy - 5 blocks to the beach, 1 block to Mason Ave.

350 yd to city/town center

Sleeps 7 pers.3 bedrooms

YardTerraceParkingInternet

Sweet Bamboo Beach Cottage

80 yd to city/town center

Sleeps 6 pers.3 bedrooms958 ft²

YardTerraceParkingInternet

Pristine Downtown 1-Bedroom Steps from State House

300 yd to city/town center

Sleeps 4 pers.1 bedroom398 ft²

Secluded Waterfront Cottage on 200 acre farm near Queenstown

3.3 mi to city/town center

Sleeps 8 pers.4 bedrooms

TerraceParkingInternet

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

Waterfront Getaway with Dock

350 yd to city/town center

Sleeps 6 pers.3 bedrooms

The Crab Shack on Carter's Creek

1.1 mi to city/town center

Sleeps 4 pers.1 bedroom840 ft²

YardTerraceParkingInternet

Cozy cottage on the Chesapeake Bay

2.4 mi to city/town center

Sleeps 6 pers.3 bedrooms990 ft²

TerraceParkingInternet

Waterfront with Private Pier and Tranquil Water views!

8.2 mi to city/town center

Sleeps 4 pers.2 bedrooms1,292 ft²

YardTerraceParkingInternet

Quaint fishing retreat on the lower Potomac Piney Pt

7.7 mi to city/town center

Sleeps 3 pers.2 bedrooms1,195 ft²

BalconyYardParkingInternet

Private Cottage on gated estate

0.6 mi to city/town center

Sleeps 5 pers.3 bedrooms

Bring the Boat & Bikes to Our in Town Kilmarnock Home from 100 per night. <br>

350 yd to city/town center

Sleeps 6 pers.3 bedrooms2,390 ft²

YardTerraceParkingInternet

Garden Cottage · Garden Cottage - Fire Pit and Grill near Beaches

1.9 mi to city/town center

Sleeps 2 pers.1 bedroom

Room on river with sunset views and private beach!

5.3 mi to city/town center

Sleeps 2 pers.1 bedroom

TerraceParkingInternet

\"Gull Cottage\" Charming Tiny House on Chesapeake Bay-Boat Launch/Slip included

6.7 mi to city/town center

Sleeps 4 pers.1 bedroom366 ft²

YardTerraceParkingInternet

One more unit available

Classic Chesapeake Beachside Cottage w/ Porch!

Holiday Home

2.2 mi to city/town center

Sleeps 4 pers.2 bedrooms1,313 ft²

YardParkingKitchenInternet

Buckroe Bungalow in Hampton

Park Place - Comfy Condo Close to Beach

Flat 207 with Fireplace in Saint Michaels

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

Waterfront Paradise on the Eastern Shore of Chesapeake Bay

Mariners Cove Waterfront - Private Dock, Pet Friendly, Wi-Fi, Off-Street Parking

Romantic Waterfront Abode with Patio & Dock!

Sunny Shores Retreat with Private Pool

Relaxation awaits! Potomac River Waterfront Home.

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

Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!

Clean and Cozy 2 Br home blocks away from downtown

Beachfront Getaway, Dolphin Suite, 🐶 💙

The Blue Crab Beach House - Free beach passes 🦀

Cozy Cottage - quaint and comfy - 5 blocks to the beach, 1 block to Mason Ave.

Sweet Bamboo Beach Cottage

Pristine Downtown 1-Bedroom Steps from State House

Secluded Waterfront Cottage on 200 acre farm near Queenstown

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

Waterfront Getaway with Dock

The Crab Shack on Carter's Creek

Cozy cottage on the Chesapeake Bay

Waterfront with Private Pier and Tranquil Water views!

Quaint fishing retreat on the lower Potomac Piney Pt

Private Cottage on gated estate

Bring the Boat & Bikes to Our in Town Kilmarnock Home from 100 per night. <br>

Garden Cottage · Garden Cottage - Fire Pit and Grill near Beaches

Room on river with sunset views and private beach!

\"Gull Cottage\" Charming Tiny House on Chesapeake Bay-Boat Launch/Slip included

Classic Chesapeake Beachside Cottage w/ Porch!

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