St. Michaels Vacation Rentals

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Vacation Rentals in St. Michaels

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

Annapolis MD

$442 nightly

$504 total

Nov 9 - Nov 10

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

Spacious 5-bedroom house with AC in gorgeous Annapolis historic district capital

Annapolis MD

With a stay at this vacation home in Annapolis (Historic District), you'll be within a 5-minute drive of Annapolis City Dock and 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

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cambridge MD

$372 nightly

$394 total

Nov 17 - Nov 18

Total with taxes and fees

A stay at this vacation home places you in the heart of Cambridge, steps from Long Wharf Park and Choptank River Lighthouse.

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

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

Historic Home with Parking Steps From Capital & USNA

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

Circa 1700 Chesapeake Colonial home on the National Register.

Stevensville MD

With a stay at this vacation home in Stevensville, you'll be next to a golf course, within a 5-minute drive of Chesapeake Bay and Matapeake State Park.

Pool

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

Cozy 2br home w/ parking in downtown Annapolis

Annapolis MD

$421 nightly

$480 total

Nov 16 - Nov 17

Total with taxes and fees

A stay at this vacation home places you in the heart of Annapolis, within a 15-minute walk of Annapolis City Dock and U.S. Naval Academy.

Kitchen

Washer

Thorneton Point Estate

Easton MD

Located in Easton, this vacation home is on the waterfront, within a 10-minute drive of Saint Michaels Village and St. Michaels Winery.

Pool

Hot Tub

Peaceful Pet-Friendly Stay - Near USNA and Beaches

Annapolis MD

With a stay at this vacation home, you'll be centrally located in Annapolis, a 4-minute drive from Chesapeake Bay and 13 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.