Holiday rentals in Tilghman Island

Find and book unique accommodation on Airbnb

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
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.
29 Aug – 5 SepIndividual Host,
€ 292 per night
4.98 out of 5 average rating, 417 reviews
Guest favourite
Guest suite in Cambridge
Oakley Suite
5 minute walk to restaurants and shops, 3 min.to the water. Ideal setting with lovely rear patio and garden with entrance to private family room. Stairs to upper level with 2 very large and private guest rooms. Landing at top of steps presents a convenience station with Keurig, microwave, and mini fridge. This Suite is completely private and includes 2 bedrooms, bath, family room, convenience station, and rear patio, all for one price! 1st floor Owners Suite available as well for a total of 8 !
27 Apr – 4 MayIndividual Host,
€ 128 per night
4.95 out of 5 average rating, 264 reviews
Guest favourite
Flat in North Beach
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.
16–23 JulIndividual Host,
€ 135 per night
4.97 out of 5 average rating, 100 reviews

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
Guest house in Stevensville
Waterfront Getaway - View of bay from your bed
29 Apr – 6 MayIndividual Host,
€ 290 per night
5.0 out of 5 average rating, 201 reviews
Guest favourite
Cabin in Lusby
Peaceful Waterfront Retreat on The Bay
13–20 SepIndividual Host,
€ 176 per night
4.91 out of 5 average rating, 202 reviews
Guest favourite
Cottage in Neavitt
The Middle Point Cottage at Saint Michaels
8–15 OctIndividual Host,
€ 445 per night
4.89 out of 5 average rating, 123 reviews
Guest favourite
Cottage in North Beach
Waterfront Cottage Near Herrington and North Beach
7–14 MayIndividual Host,
€ 256 per night
4.96 out of 5 average rating, 266 reviews
Guest favourite
Farm stay in Madison
Madison Nature Getaway
12–19 SepIndividual Host,
€ 123 per night
4.98 out of 5 average rating, 159 reviews
Superhost
Tiny home in Cambridge
Blackwater Tiny Cabin on Snakehead Creek
29 Aug – 5 SepProfessional Host,
€ 89 per night
4.89 out of 5 average rating, 491 reviews
Guest favourite
Home in Tracys Landing
The Little Gypsy BoHome
14–21 OctIndividual Host,
€ 732 per night
4.99 out of 5 average rating, 162 reviews
Guest favourite
Guest suite in Saint Michaels
Gorgeous Cottage: Easy Walk into St Michaels Town!
4–11 AugIndividual Host,
€ 164 per night
4.78 out of 5 average rating, 327 reviews
Guest favourite
Cottage in Cambridge
Church Creek - waterfront cottage & pool - private
8–15 JanIndividual Host,
€ 211 per night
4.99 out of 5 average rating, 106 reviews
Guest favourite
Guest suite in Saint Michaels
Charming Studio in the heart of St. Michael's, MD.
21–28 AprProfessional Host,
€ 380 per night
4.91 out of 5 average rating, 123 reviews
Guest favourite
Guest house in Cambridge
Rosses Chance Guest House
13–20 MayIndividual Host,
€ 238 per night
4.99 out of 5 average rating, 109 reviews
Superhost
Cottage in Wittman
Perfect St. Michaels Getaway
23–30 NovProfessional Host,
€ 161 per night
4.86 out of 5 average rating, 144 reviews

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

€ 119 before taxes and fees

Destinations to explore