St. Michaels Vacation Rentals

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Vacation Rentals in St. Michaels

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

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Annapolis MD

With a stay at this vacation home in Annapolis (Cape Saint Claire), you'll be a 2-minute drive from Chesapeake Bay and 6 minutes from Sandy Point State Park.

Pool

Kitchen

Fabulous 5-bedroom house with AC in charming Annapolis

Annapolis MD

$480 nightly

$547 total

Sep 14 - Sep 15

Total with taxes and fees

With a stay at this vacation home in Annapolis, you'll be within a 10-minute drive of U.S. Naval Academy and Annapolis City Dock.

Air conditioning

Laundry

Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything

Annapolis MD

With a stay at this vacation home, you'll be centrally located in Annapolis, steps from Annapolis City Dock and 4 minutes by foot from U.S. Naval Academy.

Kitchen

Washer

Charming Historic Annapolis Home With Two Off-street Parking Places!

Annapolis MD

With a stay at this vacation home, you'll be centrally located in Annapolis, just a 4-minute walk from Annapolis City Dock and 8 minutes by foot from U.S. Naval Academy.

Kitchen

Washer

Lovely bay views with kayaks, bikes, fire pit, crabbing & more

Shady Side MD

With a stay at this vacation home in Shady Side, you'll be within a 10-minute drive of Chesapeake Bay and Shadyside Park.

Kitchen

Washer

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Annapolis MD

A stay at this vacation home places you in the heart of Annapolis, steps from U.S. Naval Academy and Annapolis City Dock.

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

Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

St. Michaels MD

When you stay at this vacation home in St. Michaels, you'll be on the waterfront, within a 5-minute drive of Perry Cabin Park and Saint Michaels Town Hall.

Kitchen

Washer

Peaceful Pet-Friendly Stay - Near USNA and Beaches

Annapolis MD

With a stay at this vacation home, you'll be centrally located in Annapolis, within a 5-minute drive of Sandy Point State Park and Chesapeake Bay.

Kitchen

Washer

Private 2 Acre Waterfront Family Retreat with Pool & Pier

Cambridge MD

When you stay at this vacation home in Cambridge, you'll be on the waterfront and 14 minutes by car from Christ Rock Park.

Pool

Kitchen

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.