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

$570 nightly

$650 total

Aug 25 - Aug 26

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

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

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Stevensville MD

$324 nightly

$334 total

Aug 26 - Aug 27

Total with taxes and fees

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

Kitchen

Washer

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

Saint Leonard MD

$260 nightly

$276 total

Aug 31 - Sep 1

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

Stunning Chesapeake views from almost ever room, private 15 home community beach, fossils, 450 pier,crabbing,fishing

Port Republic MD

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

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

Bright and airy waterfront getaway

Benedict MD

Located in Benedict, this vacation home is on the waterfront, a 1-minute drive from Patuxent River and 7 minutes from Running Hare Vineyard.

Kitchen

Free WiFi

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

Washer

Pet-Friendly Cottage on Tilghman Island | Minutes to St. Michaels

Tilghman Island MD

Located in Tilghman, this vacation home is in a rural location, within a 15-minute walk of Kronsberg Park and Phillips Wharf Environmental Center.

Kitchen

Washer

Private Chesapeake Bay Beach community…love to feel the sand between your toes?

Port Republic MD

When you stay at this vacation home in Port Republic, you'll be on the waterfront, within a 15-minute walk of Chesapeake Bay and Northern Chesapeake Bay.

Kitchen

Washer

Beachside Oasis with Beach Passes & King Suite by A Haven Away

North Beach MD

$316 nightly

$349 total

Aug 26 - Aug 27

Total with taxes and fees

When you stay at this vacation home in North Beach, you'll be near the beach, within a 15-minute walk of Chesapeake Bay and Bayside History Museum.

Kitchen

Washer

Cottage with Private Water Access | Pet-Friendly | Near St. Michaels

Neavitt MD

When you stay at this vacation home in Neavitt, you'll be 6 minutes by foot from Neavitt Park.

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.