Tilghman Vacation Rentals

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Vacation Rentals in Tilghman

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

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

Annapolis MD

$401 nightly

$457 total

Sep 22 - Sep 23

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

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

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

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

Saint Leonard MD

$236 nightly

$250 total

Sep 23 - Sep 24

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

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

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

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

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

About Time! - Remote Waterfront Home with Dock - Sleeps 15-New EV Charger!

Taylors Island MD

With a stay at this vacation home in Taylors Island, you'll be on the waterfront, within a 10-minute drive of Chesapeake Bay and Northern Chesapeake Bay.

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

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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.