Tilghman Island vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Tilghman Island

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

Guest favorite

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.

Mar 19 – 26

R3,926 ZAR per night
Guest favorite

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.

Aug 16 – 23

R2,340 ZAR per night
Guest favorite

Apartment 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.

Nov 4 – 11

R2,472 ZAR per night

Popular amenities for Tilghman Island vacation 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 vacation rentals in Tilghman Island

Guest favorite

Apartment in Lexington Park

5.0 out of 5 average rating, 310 reviews

Adorable Waterfront Apartment Weekend Getaway

Jan 14 – 21

R1,665 ZAR per night
Superhost

Home in Cambridge

4.89 out of 5 average rating, 110 reviews

Dorothy's Chesapeake Delight

Apr 4 – 11

R2,804 ZAR per night
Guest favorite

Home in Shady Side

5.0 out of 5 average rating, 113 reviews

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

Mar 18 – 25

R9,111 ZAR per night
Guest favorite

Cottage in North Beach

4.96 out of 5 average rating, 268 reviews

Waterfront Cottage Near Herrington and North Beach

May 1 – 8

R3,683 ZAR per night
Guest favorite

Guesthouse in Stevensville

5.0 out of 5 average rating, 202 reviews

Waterfront Getaway - View of bay from your bed

Nov 8 – 15

R5,351 ZAR per night
Guest favorite

Home in Tracys Landing

4.99 out of 5 average rating, 162 reviews

The Little Gypsy BoHome

Oct 12 – 19

R13,023 ZAR per night
Superhost

Tiny home in Cambridge

4.89 out of 5 average rating, 492 reviews

Blackwater Tiny Cabin on Snakehead Creek

Nov 29 – Dec 6

R1,593 ZAR per night
Guest favorite

Cottage in Cambridge

4.99 out of 5 average rating, 107 reviews

Church Creek - waterfront cottage & pool - private

Feb 28 – Mar 7

R3,900 ZAR per night
Guest favorite

Cottage in Neavitt

4.89 out of 5 average rating, 123 reviews

The Middle Point Cottage at Saint Michaels

Oct 6 – 13

R8,367 ZAR per night
Guest favorite

Guesthouse in Grasonville

4.9 out of 5 average rating, 202 reviews

Eastern Shore Charm on Winchester Creek

Aug 21 – 28

R2,511 ZAR per night
Guest favorite

Cabin in Lusby

4.93 out of 5 average rating, 138 reviews

Hideaway on the Bay: Waterfront Vintage A Frame

Jul 14 – 21

R6,166 ZAR per night
Guest favorite

Home in Cambridge

4.99 out of 5 average rating, 134 reviews

Sunset Breezes - quiet waterfront retreat

Oct 22 – 29

R5,927 ZAR per night

Other great vacation rentals in Tilghman Island

Guest favorite

Cottage in California

4.97 out of 5 average rating, 190 reviews

Cozy Little Cottage

Apr 30 – May 7

R1,680 ZAR per night
Guest favorite

Home in Saint Michaels

4.91 out of 5 average rating, 151 reviews

Small Historic House Downtown St Michaels

Dec 21 – 28

R3,623 ZAR per night
Guest favorite

Guest suite in Cambridge

4.95 out of 5 average rating, 265 reviews

Oakley Suite

Nov 17 – 24

R2,802 ZAR per night
Guest favorite

Cottage in Saint Leonard

4.99 out of 5 average rating, 101 reviews

Captain Jack's Bay Hideaway

Sep 3 – 10

R2,918 ZAR per night
Guest favorite

Apartment in Church Creek

4.97 out of 5 average rating, 369 reviews

Church Creek Natures' Rest

Dec 6 – 13

R2,485 ZAR per night
Guest favorite

Guest suite in Lusby

4.99 out of 5 average rating, 299 reviews

Riverfront Chalet Kayak/Canoe, pier, breakfast!

Feb 25 – Mar 4

R2,455 ZAR per night
Guest favorite

Guesthouse in Annapolis

4.9 out of 5 average rating, 202 reviews

Calico Cottage Guest House, king bed, free parking

Nov 14 – 21

R1,853 ZAR per night
Guest favorite

Guesthouse in Galesville

4.95 out of 5 average rating, 163 reviews

Gorgeous water view studio!

Jun 29 – Jul 6

R3,522 ZAR per night
Guest favorite

Apartment in Saint Michaels

4.91 out of 5 average rating, 124 reviews

Charming Studio in the heart of St. Michael's, MD.

Aug 22 – 29

R7,535 ZAR per night
Guest favorite

Home in Tilghman Island

4.97 out of 5 average rating, 32 reviews

Tilghman Retreat: A house on the Chesapeake Bay.

Apr 22 – 29

R7,869 ZAR per night
Guest favorite

Guesthouse in Cambridge

5.0 out of 5 average rating, 12 reviews

Camelot Cottage

Jun 10 – 17

R1,777 ZAR per night
Guest favorite

Guesthouse in Oxford

4.99 out of 5 average rating, 81 reviews

The Nichols House Cottage

Jul 25 – Aug 1

R2,637 ZAR per night

Quick stats about vacation 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

R2,462 ZAR before taxes and fees

Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Tilghman Island?

    Yes! Work meets play with ease at over 10 vacation rentals in Tilghman Island featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Tilghman Island have wifi?

    Absolutely! We offer over 10 house rentals with wifi in Tilghman Island. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Tilghman Island?

    Tilghman Island has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Tilghman Island?

    Experience the best of Tilghman Island with our house rentals, starting at about $160 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Tilghman Island have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Tilghman Island. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Tilghman Island?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore