Chesapeake Beach Vacation Rentals

Name: Private Waterfront Retreat with Pool, Hot Tub and Game Room
Address: Tracys Landing

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Vacation Rentals in Chesapeake Beach

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

This vacation home is 3.1 mi (5 km) from Upper Yough River and 4.8 mi (7.7 km) from Bayside History Museum.

Calloway Drive Retreat | House in Shady Side

When you stay at this vacation home in Shady Side, you'll be near the beach and 5 minutes by car from Franklin Point State Park.

Dollhouse in Central Historic St Michaels

With a stay at this vacation home in St. Michaels, you'll be within a 10-minute walk of Chesapeake Bay Maritime Museum and St. Michaels Museum.

Private Waterfront Woods | Dock, Kayaks, Views

With a stay at this vacation home in Annapolis, you'll be on the beach, within a 15-minute drive of U.S. Naval Academy and Bay Bridge Market Place Shopping Center.

Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!

With a stay at this vacation home in St. Leonard, you'll be near the beach, just steps from Jefferson Patterson Park and Museum and a 3-minute drive from Perigeaux Vineyards and Winery.

La Maison - Stunning waterfront views with pool

With a stay at this vacation home in Annapolis (Cape St. John), you'll be within a 15-minute drive of U.S. Naval Academy and Broad Creek Marsh.

Brand New Spacious Luxury Home

With a stay at this vacation home in Annapolis, you'll be within a 5-minute drive of U.S. Naval Academy and Spa Creek.

Relax on Kent Island in 3 Bedroom Home w/Waterview

$255

includes taxes & fees

$241 per night

Jan 5 - Jan 6, 2025

Located in Stevensville, this vacation home is within a 15-minute drive of Matapeake State Park and Paul Reed Smith Guitars.

Walk to Everything House

With a stay at this vacation home in St. Michaels, you'll be within a 10-minute walk of Chesapeake Bay Maritime Museum and St. Michaels Museum.

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

With a stay at this vacation home in Royal Oak, you'll be on the waterfront, and 8.3 mi (13.3 km) from St. Michaels Winery and 8.4 mi (13.6 km) from St. Michaels Museum.

Serene waterfront sunsets in this sprawling historic Annapolis home

With a stay at this vacation home in Annapolis (Hillsmere), you'll be within a 15-minute drive of U.S. Naval Academy and Maryland Quiet Waters Park.

Private Waterfront Retreat with Pool, Hot Tub and Game Room

Located in Tracys Landing, this vacation home is on the waterfront, within a 15-minute drive of Upper Yough River and Bayside History Museum.

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.