Tilghman Island vacation rentals

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Top-rated vacation rentals in Tilghman Island

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

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Guest favorite

Cottage in Saint Michaels

4.98 out of 5 average rating, 425 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.

Nov 15 – 22

G$42,676 GYD per night

Guest favorite

Farm stay in Madison

4.98 out of 5 average rating, 162 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.

Mar 7 – 14

G$25,766 GYD per night

Superhost

Tiny home in Cambridge

4.89 out of 5 average rating, 496 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!

Nov 9 – 16

G$18,153 GYD per night

Guest favorite

Home in Shady Side

5.0 out of 5 average rating, 116 reviews

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

The Cottage at Silverwater is a lesson in quiet luxury, compelling architecture, unimaginable views and endless comforts. Original fine art and luxe bedding envelope you in a modern, light-filled space. Outside you will be treated to an expansive waterfront lawn that is great for games and afternoon sun. Rest on modern lounges or watch the sunset on your private waterfront bluestone patio tucked into the sea grass. As a guest favorite, your fabulous getaway is here—just read the reviews!

Feb 11 – 18

G$92,422 GYD per night

Guest favorite

Apartment in North Beach

4.97 out of 5 average rating, 102 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 16 – 23

G$27,341 GYD per night

Guest favorite

Guesthouse in Easton

4.99 out of 5 average rating, 545 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.

Jan 25 – 30

G$29,946 GYD per night

Guest favorite

Cottage in Saint Michaels

4.99 out of 5 average rating, 136 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.

Sep 15 – 22

G$111,584 GYD 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

Oct 23 – 30

G$30,120 GYD per night

Guest favorite

Apartment in Lexington Park

5.0 out of 5 average rating, 315 reviews

Adorable Waterfront Apartment Weekend Getaway

Bright & cheery 1 bedroom waterfront apartment nestled on the banks of the St. Mary's River. Amazing, dreamy views. It's a sweet spot to relax and enjoy a quiet get-away or launch a kayak, take a walk, enjoy great food cuisine. We sit next to St. Mary's College of MD and Historic St. Mary's City. You may see college sailing races, crew teams rowing, or the historic Maryland Dove sailing down the river. It's lovely here fall, winter, spring, summer! SUNSETS!

Oct 1 – 8

G$18,327 GYD per night

Guest favorite

Cottage in Saint Michaels

4.98 out of 5 average rating, 174 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.

Aug 13 – 20

G$54,856 GYD per night

Guest favorite

Tiny home in Cambridge

4.99 out of 5 average rating, 156 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.

Aug 21 – 28

G$22,299 GYD 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!

Gorgeous, sunny former artist loft with great views. Across from Miles River & harbor. Walk to town! Shopping, brewery, winery, museum, restaurants await! Located in historic Bentley Hay, the lodge is perfect for relaxing walks while runners and bikers explore spectacular sights, including the nearby St Michaels Nature Trail. Or rent a kayak and explore San Domingo Creek! NO PETS OR SMOKING. 4 GUESTS MAX BY LAW. Talbot Co License STR-716-KIM

Oct 21 – 28

G$29,104 GYD 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

Guesthouse in Annapolis

4.9 out of 5 average rating, 206 reviews

Calico Cottage Guest House, king bed, free parking

Jan 10 – 17

G$20,406 GYD per night

Guest favorite

Guest suite in Lusby

4.99 out of 5 average rating, 303 reviews

Riverfront Chalet Kayak/Canoe, pier, breakfast!

Mar 20 – 27

G$26,597 GYD per night

Guest favorite

Apartment in Lusby

4.96 out of 5 average rating, 165 reviews

Terrace Suite - Private Flat in Historic Manor.

May 27 – Jun 3

G$27,512 GYD per night

Superhost

Cottage in Wittman

4.9 out of 5 average rating, 135 reviews

"Wittman Cottage"

Mar 24 – 31

G$53,952 GYD per night

Guest favorite

Guesthouse in Stevensville

5.0 out of 5 average rating, 207 reviews

Waterfront Getaway - View of bay from your bed

Jan 10 – 17

G$59,912 GYD per night

Guest favorite

Cottage in California

4.97 out of 5 average rating, 193 reviews

Cozy Little Cottage

Sep 7 – 14

G$18,502 GYD per night

Guest favorite

Guest suite in Cambridge

4.96 out of 5 average rating, 267 reviews

Oakley Suite

Sep 8 – 15

G$28,053 GYD per night

Guest favorite

Cottage in Saint Leonard

4.99 out of 5 average rating, 101 reviews

Captain Jack's Bay Hideaway

Oct 2 – 9

G$31,680 GYD per night

Show all

Other great vacation rentals in Tilghman Island

Guest favorite

Apartment in Church Creek

4.97 out of 5 average rating, 371 reviews

Church Creek Natures' Rest

Feb 19 – 26

G$27,361 GYD per night

Guest favorite

Guesthouse in Annapolis

4.97 out of 5 average rating, 197 reviews

RECENTLY RENOVATED Cottage Near Downtown Annapolis

Oct 21 – 28

G$25,189 GYD per night

Guest favorite

Cabin in Lusby

4.91 out of 5 average rating, 209 reviews

Peaceful Waterfront Retreat on The Bay

Sep 16 – 23

G$36,134 GYD per night

Guest favorite

Guesthouse in Lusby

4.97 out of 5 average rating, 136 reviews

Cozy Lakeside Studio Retreat.

Jul 29 – Aug 5

G$27,018 GYD per night

Guest favorite

Guesthouse in Grasonville

4.9 out of 5 average rating, 203 reviews

Eastern Shore Charm on Winchester Creek

Oct 2 – 9

G$27,439 GYD per night

Guest favorite

Cottage in Neavitt

4.9 out of 5 average rating, 124 reviews

The Middle Point Cottage at Saint Michaels

Apr 9 – 16

G$92,124 GYD 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.

Jul 27 – Aug 3

G$99,787 GYD per night

Guest favorite

Guesthouse in Cambridge

5.0 out of 5 average rating, 13 reviews

Camelot Cottage

Oct 6 – 13

G$18,344 GYD 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
G$31,273 GYD 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 wifi, over 10 homes with air conditioning, 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

Guesthouse in Annapolis

Guest suite in Lusby

Apartment in Lusby

Cottage in Wittman

Guesthouse in Stevensville

Cottage in California

Guest suite in Cambridge

Cottage in Saint Leonard

Other great vacation rentals in Tilghman Island

Apartment in Church Creek

Guesthouse in Annapolis

Cabin in Lusby

Guesthouse in Lusby

Guesthouse in Grasonville

Cottage in Neavitt

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