Tilghman Island vacation rentals

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Top-rated vacation rentals in Tilghman Island

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Guest favorite

Farm stay in Madison

4.98 out of 5 average rating, 163 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.

Jul 27 – Aug 3

ﺩ.ﺇ466 per night

Guest favorite

Cottage in Saint Michaels

4.98 out of 5 average rating, 426 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 28 – Apr 4

ﺩ.ﺇ765 per night

Superhost

Tiny home in Cambridge

4.89 out of 5 average rating, 497 reviews

Blackwater Tiny Cabin on Snakehead Creek

The Solar Powered Tiny Cabin is located on a farmette 5 min away from Blackwater Refuge! It is an affordable and unique way to visit and enjoy all that Cambridge and Blackwater Refuge have to offer! Staying the cabin will make your visit even more memorable!The Tiny Cabin is now located 50 steps away from Pitcher Dam Creek which leads to the Little Blackwater! Kayaks on site! Bring your fishing rod to catch popular Snakeheads! 15 minute drive to Route 50, downtown Cambridge, shopping and dining!

Sep 25 – Oct 2

ﺩ.ﺇ314 per night

Guest favorite

Apartment in North Beach

4.96 out of 5 average rating, 103 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.

Oct 21 – 28

ﺩ.ﺇ489 per night

Guest favorite

Cottage in Saint Leonard

4.99 out of 5 average rating, 102 reviews

Captain Jack's Bay Hideaway

This beach cottage sits just across the street from the Chesapeake Bay on the Western Shore. You'll have access to two private community beaches where you can sit, relax, and just enjoy the scenery. If you are an early riser, you can enjoy beautiful sun rises over the bay. If you search the sand, you might even find fossils, including shark teeth! Close proximity to Washington DC, Annapolis, and Baltimore. There are a lot of local restaurants and shopping. You will not be disappointed.

May 6 – 13

ﺩ.ﺇ542 per night

Guest favorite

Guesthouse in Easton

4.99 out of 5 average rating, 546 reviews

Chill in The Crib! Easton, Maryland

Welcome to Maryland's Eastern Shore and your own private space in a converted corn crib, complete with the comforts of home. The space includes a vaulted ceiling, queen-sized Casper® mattress, quality linens, heat & AC, wireless Internet, a coffee counter, stocked bar fridge, full bath w/ shower (includes quality bath supplies), and a private entrance. Our space is permitted for two individuals (No children under 8 years of age.), and please limit your visit to one vehicle only.

Dec 12 – 17

ﺩ.ﺇ527 per night

Guest favorite

Cottage in Saint Michaels

4.99 out of 5 average rating, 137 reviews

La Casita on Harris Creek, St. Michaels

Newly constructed architecturally unique guesthouse inspired by the historic barns of the Chesapeake. Stay in luxury on a secluded 40 acre farm on Harris Creek, be at one with nature & still only 5 min from town's fine dining, shops & charm . With 360 views, TV/Wi-fi, full bath/shower, galley kitchen w/ microwave, fridge w/ice maker, washer/drier, patio fire pit, private pool & kayaks. We comply with Talbot County's zoning that requires a 3 night minimum ST-934-HUD 2020.

Jul 25 – Aug 1

ﺩ.ﺇ2,049 per night

Guest favorite

Guest suite in Tilghman Island

4.96 out of 5 average rating, 114 reviews

Black Walnut Cove Retreat, Tilghman Island

Our waterfront studio retreat is a birdwatchers paradise. Located on beautiful Black Walnut Cove at the southern tip of Tilghman Island, you will be in a quiet neighborhood surrounded by water. Enjoy a quiet walk or bike ride along the Chesapeake Bay shoreline. You will have access to our dock and small boat ramp. Crabbing and fishing are a delight. Please note: 1) There is a 3-nt. minimum on holiday weekends. 2) Children between the ages of 1 and 5 are not permitted

Aug 3 – 10

ﺩ.ﺇ543 per night

Guest favorite

Guesthouse in Stevensville

5.0 out of 5 average rating, 208 reviews

Waterfront Getaway - View of bay from your bed

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

Oct 25 – Nov 1

ﺩ.ﺇ991 per night

Guest favorite

Cottage in Saint Michaels

4.98 out of 5 average rating, 176 reviews

The Little Anchor Cottage, St. Michaels, MD

Welcome to the Little Anchor cottage in St. Michaels, Maryland! The cottage was built in late 1880s and is located in the charming Historic District, where you can enjoy the convenience of walking one block to the downtown shops and restaurants on S. Talbot street. And for another 5 to 15 minute walk, you can reach more waterfront dining on St. Michaels Harbor with its boat slips, boat ramps, the Chesapeake Bay Maritime Museum, Muskrat Park and Hollis Park.

Jan 21 – 28

ﺩ.ﺇ864 per night

Guest favorite

Tiny home in Cambridge

4.99 out of 5 average rating, 157 reviews

Blackwater Refuge House on The Farm, water access

The Little House on The Farm is located on a beautiful family farm in rural Dorchester County! Located just 1.5 miles from the Blackwater Wildlife Refuge and Harriet Tubman National Park, This space is quaint,yet provides all the basics for a cozy welcoming getaway! Bring your bikes and cycle to the refuge and kayak in the Blackwater River. Kitchen is fully stocked for cooking. Coffee, tea and basic condiments and all linens and towels are provided.

Jul 25 – Aug 1

ﺩ.ﺇ393 per night

Guest favorite

Home in Cambridge

4.92 out of 5 average rating, 180 reviews

Guest House: Farm homestead

Quiet country guest house with 1 BR/ 1 BA, queen sleeper sofa and fully stocked kitchen. Coffee/creamer/sugar provided. Come relax & enjoy the row boat and paddle boat, fishing in the ponds (C&R, No Pond Access from August 24 thru January 30 annually), grill on the deck, watch the bikers roll by (Ironman course) or finish your day by the fire-pit with s'mores! All this and only 3 miles to town and on the Eagle Man and Iron Man race course.

Sep 10 – 17

ﺩ.ﺇ458 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Tilghman Island vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

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

Guest suite in Lusby

4.99 out of 5 average rating, 303 reviews

Riverfront Chalet Kayak/Canoe, pier, breakfast!

Dec 9 – 16

ﺩ.ﺇ456 per night

Guest favorite

Home in Cambridge

4.99 out of 5 average rating, 142 reviews

Sunset Breezes - quiet waterfront retreat

Jan 28 – Feb 4

ﺩ.ﺇ1,574 per night

Guest favorite

Home in Shady Side

5.0 out of 5 average rating, 117 reviews

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

Dec 26 – Jan 2

ﺩ.ﺇ1,972 per night

Guest favorite

Guest suite in Saint Michaels

4.78 out of 5 average rating, 330 reviews

Gorgeous Cottage: Easy Walk into St Michaels Town!

Sep 20 – 27

ﺩ.ﺇ513 per night

Guest favorite

Condo in Oxford

4.98 out of 5 average rating, 112 reviews

Cozy Oxford Getaway

Mar 7 – 14

ﺩ.ﺇ714 per night

Guest favorite

Guesthouse in Annapolis

4.97 out of 5 average rating, 197 reviews

RECENTLY RENOVATED Cottage Near Downtown Annapolis

Mar 16 – 23

ﺩ.ﺇ427 per night

Guest favorite

Home in Saint Michaels

4.9 out of 5 average rating, 156 reviews

Small Historic House Downtown St Michaels

Mar 2 – 9

ﺩ.ﺇ703 per night

Guest favorite

Cottage in Neavitt

4.9 out of 5 average rating, 124 reviews

The Middle Point Cottage at Saint Michaels

Apr 17 – 24

ﺩ.ﺇ1,623 per night

Show all

Other great vacation rentals in Tilghman Island

Guest favorite

Cottage in California

4.97 out of 5 average rating, 195 reviews

Cozy Little Cottage

Apr 20 – 27

ﺩ.ﺇ326 per night

Guest favorite

Guesthouse in Annapolis

4.9 out of 5 average rating, 208 reviews

Calico Cottage Guest House, king bed, free parking

Mar 16 – 23

ﺩ.ﺇ360 per night

Guest favorite

Home in Tracys Landing

4.99 out of 5 average rating, 166 reviews

The Little Gypsy BoHome

Dec 12 – 19

ﺩ.ﺇ1,687 per night

Guest favorite

Guesthouse in Cambridge

4.99 out of 5 average rating, 109 reviews

Rosses Chance Guest House

Aug 24 – 31

ﺩ.ﺇ901 per night

Guest favorite

Guesthouse in Riva

4.99 out of 5 average rating, 273 reviews

The Riva House

Dec 6 – 13

ﺩ.ﺇ535 per night

Superhost

Cottage in Wittman

4.86 out of 5 average rating, 145 reviews

Perfect St. Michaels Getaway

Jul 30 – Aug 6

ﺩ.ﺇ953 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.

Sep 6 – 13

ﺩ.ﺇ1,758 per night

Guest favorite

Guesthouse in Cambridge

5.0 out of 5 average rating, 13 reviews

Camelot Cottage

Oct 19 – 26

ﺩ.ﺇ323 per night

Show all

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
10 properties are a good fit for families
Total number of reviews
310 reviews
Nightly prices starting at
ﺩ.ﺇ551 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 10 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 $150 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 air conditioning, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Tilghman Island vacation rentals

Top-rated vacation rentals in Tilghman Island

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Tilghman Island vacation rentals

Stay near Tilghman Island's top sights

Other great vacation rentals in Tilghman Island

Guest suite in Lusby

Home in Cambridge

Home in Shady Side

Guest suite in Saint Michaels

Condo in Oxford

Guesthouse in Annapolis

Home in Saint Michaels

Cottage in Neavitt

Other great vacation rentals in Tilghman Island

Cottage in California

Guesthouse in Annapolis

Home in Tracys Landing

Guesthouse in Cambridge

Guesthouse in Riva

Cottage in Wittman

Home in Tilghman Island

Guesthouse in Cambridge

Quick stats about vacation rentals in Tilghman Island

Total rentals

Wifi availability

Rentals with dedicated workspaces

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

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

Do house rentals in Tilghman Island have wifi?

Are there family-friendly house rentals in Tilghman Island?

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

Do house rentals in Tilghman Island have air conditioning?

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

Destinations to explore