Holiday rentals in Tilghman Island

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Top-rated holiday rentals in Tilghman Island

Guests agree: these stays are highly rated for location, cleanliness and more.

Guest favourite

Cottage in Saint Michaels

4.98 out of 5 average rating, 418 reviews

St. Michaels-Historic Dist. Margaret Wells House

The Margaret Wells House is in the heart of the Historic District between the main street and water. Enjoy a total renovation of this charming home. A short walk to the water's edge, Inn at Perry Cabin, Chesapeake Bay Maritime Museum, restaurants, shops, winery, brewery and local market. A perfect spot for a couple's Shore weekend getaway or attending a wedding, nearby. Our nightly pricing includes coffee, tea, fresh linens on beds, hand-milled natural soap, fresh bath towels and wash cloths.

21–28 Mar

€ 218 per night
Guest favourite

Farm stay in Madison

4.98 out of 5 average rating, 159 reviews

Madison Nature Getaway

We're on 106 acres minutes away from Cambridge, Blackwater NWR, Harriet Tubman URR State Park and two public boat ramps for access to Chesapeake Bay. Hike our trails and enjoy bird watching, wildlife photography and fishing on our award winning tree farm and relax by our pond. Bring your bikes, binoculars and kayaks and enjoy the surrounding area. We have a gas grill and a screened pavilion for our guests for parties and meals. FRIENDS OF BLACKWATER NWR MEMBERS & MILITARY RECEIVE A 10% DISCOUNT.

22–29 Oct

€ 124 per night
Guest favourite

Flat in North Beach

4.97 out of 5 average rating, 100 reviews

Bayside Oasis of Southern Maryland

1 1/2 blocks from the beautiful Chesapeake Bay. Walk to boardwalk, restaurants and shopping. Beach opens, with some restrictions, May 28, 2021. Free beach pass provided. Quiet friendly town where everyone knows your name. King bed, private bath with shower (no tub). Free WiFi, private off street parking, 45” TCL-Roku TV, Echo Dot, Keurig w/pods for coffee and tea, full kitchen (no dishwasher), beach chairs, beach towels, dishes, flatware, pots pans. Chesapeake Beach is 1-mile south on Rt 262.

14–21 Mar

€ 136 per night

Popular amenities for Tilghman Island holiday rentals

Stay near Tilghman Island's top sights

Wylder Hotel Tilghman Island3 locals recommend
Characters Bridge Restaurant5 locals recommend
Two if by Sea6 locals recommend
Marker 55 locals recommend
Tilghman Island Marina & Rentals7 locals recommend
Tilghman Watermen's Museum3 locals recommend

Other great holiday rentals in Tilghman Island

Guest favourite

Cottage in Deale

4.95 out of 5 average rating, 137 reviews

Chesapeake Bay Cottage

5–12 Nov

€ 309 per night
Guest favourite

Guest house in Stevensville

5.0 out of 5 average rating, 202 reviews

Waterfront Getaway - View of bay from your bed

17–24 Apr

€ 264 per night
Guest favourite

Home in Tracys Landing

4.99 out of 5 average rating, 162 reviews

The Little Gypsy BoHome

21–28 Nov

€ 568 per night
Guest favourite

Cabin in Lusby

4.91 out of 5 average rating, 203 reviews

Peaceful Waterfront Retreat on The Bay

22–29 Oct

€ 173 per night
Guest favourite

Cottage in North Beach

4.96 out of 5 average rating, 268 reviews

Waterfront Cottage Near Herrington and North Beach

1–8 May

€ 225 per night
Guest favourite

Flat in Lexington Park

5.0 out of 5 average rating, 310 reviews

Adorable Waterfront Apartment Weekend Getaway

17–24 Jan

€ 94 per night
Superhost

Tiny home in Cambridge

4.89 out of 5 average rating, 492 reviews

Blackwater Tiny Cabin on Snakehead Creek

7–14 Jul

€ 87 per night
Guest favourite

Guest suite in Cambridge

4.95 out of 5 average rating, 265 reviews

Oakley Suite

23–30 Aug

€ 139 per night
Guest favourite

Home in Shady Side

5.0 out of 5 average rating, 113 reviews

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

2–9 Jul

€ 1,090 per night
Guest favourite

Cottage in Neavitt

4.89 out of 5 average rating, 123 reviews

The Middle Point Cottage at Saint Michaels

4–11 Mar

€ 449 per night
Guest favourite

Cottage in Cambridge

4.99 out of 5 average rating, 107 reviews

Church Creek - waterfront cottage & pool - private

8–15 Sep

€ 223 per night
Guest favourite

Guest house in Grasonville

4.9 out of 5 average rating, 202 reviews

Eastern Shore Charm on Winchester Creek

1–8 Apr

€ 126 per night

Quick stats about holiday rentals in Tilghman Island

Total rentals

20 properties

Wifi availability

20 properties include access to wifi

Rentals with dedicated workspaces

10 properties have a dedicated workspace

Family-friendly rentals

20 properties are a good fit for families

Total number of reviews

300 reviews

Nightly prices starting at

€ 120 before taxes and fees

Destinations to explore