Chesapeake Beach Vacation Rentals

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Vacation Rentals in Chesapeake Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Annapolis MD

$463 nightly

$528 total

Oct 20 - Oct 21

Total with taxes and fees

With a stay at this vacation home in Annapolis (Arundel on the Bay), you'll be within a 15-minute drive of Chesapeake Bay and Annapolis City Dock.

Hot Tub

Kitchen

Dollhouse in Central Historic St Michaels

St Michaels MD

With a stay at this vacation home in St. Michaels (Downtown St. Michaels), you'll be within a 5-minute walk of Muskrat Park and Higgins Yacht Yard and Marina.

Kitchen

Washer

3-bedroom house in soothing Saint Leonard with AC for relaxing stays

Saint Leonard MD

$245 nightly

$260 total

Oct 6 - Oct 7

Total with taxes and fees

With a stay at this vacation home in St. Leonard, you'll be a 5-minute walk from Chesapeake Bay and 5 minutes by foot from Flag Harbor Marina.

Kitchen

Washer

Grace Cottage, St Michaels Walk to everything!

Saint Michaels MD

A stay at this vacation home places you in the heart of St. Michaels, steps from Muskrat Park and Saint Marys Square.

Kitchen

Washer

Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view

Annapolis MD

When you stay at this vacation home in Annapolis, you'll be on the beach, a 1-minute drive from Chesapeake Bay and 10 minutes from Annapolis City Dock.

Kitchen

Free WiFi

House on the Bay with Private Beach Access & Panoramic Bridge Views

Stevensville MD

When you stay at this vacation home in Stevensville, you'll be on the beach, just steps from Chesapeake Bay and Northern Chesapeake Bay.

Kitchen

Washer

Beautiful 3 Bedroom Retreat walking distance to Downtown St. Michaels

Saint Michaels MD

A stay at this vacation home places you in the heart of St. Michaels, within a 10-minute walk of Classic Motor Museum and Windon Distilling.

Kitchen

Washer

Welcome to Hickory House on the Chesapeake Bay!

Saint Leonard MD

When you stay at this vacation home in St. Leonard, you'll be near the beach, just steps from Chesapeake Bay and 5 minutes by foot from Flag Harbor Marina.

Kitchen

Washer

Home by the Bay: Chesapeake Bay Western Shore

Port Republic MD

With a stay at this vacation home in Port Republic, you'll be steps from Chesapeake Bay and Northern Chesapeake Bay.

Washer

Dryer

Rose Haven Coastal Cottage

North Beach MD

$380 nightly

$433 total

Oct 6 - Oct 7

Total with taxes and fees

With a stay at this vacation home in North Beach, you'll be within a 15-minute walk of Chesapeake Bay and Northern Chesapeake Bay.

Kitchen

Washer

Secluded Riverfront Retreat on 100+ Acre Farm in Mechanicsville, WiFi, AC, &More

Mechanicsville MD

With a stay at this vacation home in Mechanicsville, you'll be within a 15-minute drive of John Baggett Park at Laurel Grove and Laurel Ridge Park.

Kitchen

Washer

Private Cottage on gated estate

Annapolis MD

With a stay at this vacation home in Annapolis, you'll be a 2-minute drive from Chesapeake Bay and 10 minutes from Annapolis City Dock.

Kitchen

Washer

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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.