Two people in a red canoe on a body of water with a sunset and a bridge in the background.

Tilghman Vacation Rentals

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Dates

November 2026

December 2026

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Our top choices for Tilghman vacation rentals

A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

1. Beachside Oasis with Beach Passes & King Suite by A Haven Away

North Beach

Johanna S.

$277 nightly

Nov 12 - Nov 13

Total with taxes and fees

A modern kitchen with a central island, stainless steel appliances, and a window with butterfly decals.

2. The Cozy Crab- Your Charming Haven in Lovely North Beach!

North Beach

James L.

$292 nightly

Nov 12 - Nov 13

Total with taxes and fees

A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

3. WATERFRONT!! HOT TUB 3 bedroom Oasis on 2+ acres - Sleeps 8

Cambridge

Jill C.

$416 nightly

Nov 12 - Nov 13

Total with taxes and fees

A house with a yellow door and a window with a lamp outside.

4. Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Deale

Maude H.

$286 nightly

Nov 15 - Nov 16

Total with taxes and fees

A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

5. Relax on Kent Island in 4 Bedroom Home w/Waterview

Stevensville

Anthony P.

$276 nightly

Nov 15 - Nov 16

Total with taxes and fees

A lakeside view from a deck with a wooden railing, a sandy area with a boat, and a dock extending into the water.

6. 2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.

Cambridge

$244 nightly

Nov 13 - Nov 14

Total with taxes and fees

An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

7. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

North Beach

Sarah

$421 nightly

Nov 16 - Nov 17

Total with taxes and fees

8. Family Beach House: Spacious Deck, Grill & Views

Chesapeak beach

Ben W.

$354 nightly

Dec 2 - Dec 3

Total with taxes and fees

A living room with a sofa, coffee table, fireplace, and artwork on the wall.

9. 3-bedroom house in Deale located on Bay many amenities and great views

Deale

"Everything at this location was as shown on the listing and it was very clean. We were very satisfied with all elements of this stay. We were there for a weekend and did not use the place heavily, but it suited our needs. It's a quiet location. They had all the major points covered. The only negative comment I have is that the water out of the tap was smelly. I suggest bringing a couple of bottles of water and not drinking the water out of the taps. This is obviously a well maintained home...

Amelia

$383 nightly

Nov 13 - Nov 14

Total with taxes and fees

Three Adirondack chairs facing a beach with a clear view of the ocean.

10. Plum Point Cottage #14

Huntingtown

Yonnick H.

$484 nightly

Nov 12 - Nov 13

Total with taxes and fees

A lighthouse with a white exterior, a balcony, and a metal roof.

11. Charming Coastal/Country Home w/3 Acres & Sauna!

Stevensville

Michael V.

$276 nightly

Nov 12 - Nov 13

Total with taxes and fees

12. Plum Point Cottage #17

Huntingtown

$409 nightly

Nov 12 - Nov 13

Total with taxes and fees

13. Plum Point Cottage #15

Maryland

$510 nightly

Nov 12 - Nov 13

Total with taxes and fees

A living room with two grey sofas, a coffee table, and a ceiling fan.

14. Cambridge Apt in Walkable Neighborhood

Cambridge

LOIS

$291 nightly

Nov 14 - Nov 15

Total with taxes and fees

15. EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places

Easton

Lynn G.

$379 nightly

Nov 16 - Nov 17

Total with taxes and fees

A deck with a view of a marina, including boats and docks.

16. Cass-N-Reel Luxury Houseboat

Grasonville

Yamilet

$232 nightly

Nov 12 - Nov 13

Total with taxes and fees

A deck with outdoor furniture, a red door, and a house with windows.

17. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

Shady Side

"the house was clean and fully stocked with all linens. there are some staples in the refrigerator and cabinets. All cookware and eatery are provided. there is only one grocery store in the area, so plan ahead. Fast food is not readily available. Nick responded quickly and thoroughly to all messages, that was great. It's a quiet neighborhood. It was the perfect place for a family and pet. we will return"

Jenny A.

$315 nightly

Nov 16 - Nov 17

Total with taxes and fees

A spacious living room with a grey sectional sofa, a round wooden coffee table, and a patterned rug.

18. Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Prince Frederick

Sean B.

$374 nightly

Nov 20 - Nov 21

Total with taxes and fees

A modern kitchen with a large window, a dishwasher, and a ceiling fan.

19. Sunset Cottage - West River Access and Views!

Shady Side

Michelle H.

$431 nightly

Dec 1 - Dec 2

Total with taxes and fees

20. Cambridge Apt in Walkable Neighborhood

Cambridge

Anonymous traveler

$282 nightly

Nov 14 - Nov 15

Total with taxes and fees

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Find vacation rentals that suit your style

Top Tilghman Hotel Reviews

A kayak on a calm body of water with two people paddling.

Knapps Narrows Marina & Inn

Sherwood

10/10 Excellent

Stan and Joan

A waterfront property with a covered patio, a dock, and a boat.

Wylder Tilghman Island

Tilghman

10/10 Excellent

We had a great time at the Wylder Inn on Tilghman Island (20-21 May). This is a great spot for a quick getaway, and there are many things to do on site and in the area if you want to stay longer. The staff was welcoming and responsive from our arrival to departure when our key was collected from our car so we didn't have to get out in the rain. The Continental Breakfast had a variety of items to start the day right and the fire pits provided a relaxing venue at the end of the day. We look...

Alan

A room with a fireplace, a dining area with chairs, a large window with a view of the outside, and a cabinet with bottles.

Inn at Perry Cabin

Downtown St. Michaels

10/10 Excellent

Norm

St Michaels Inn

St. Michaels

10/10 Excellent

Lori

A gazebo with a dome, surrounded by a white fence, near a waterfront with a clear sky.

Rod 'N' Reel Resort

Chesapeake Beach

10/10 Excellent

Huge resort in a small, well kept town! Our room was right on the bay and was clean and nice. The beds and pillows were super comfortable. There is not a place for breakfast but if you go a little further south on the main road, there is a shopping center with a McDonalds (and a CVS and some other things)... We were in a hurry to get home so did not try any of the breakfast places that the desk clerk recommended. The staff guy that checked us in was SUPER nice and helpful!

Kathie

A Victorian-style building with a prominent tower, a porch with outdoor seating, and a sign indicating it is a bed and breakfast.

Parsonage Inn

Downtown St. Michaels

10/10 Excellent

A modern kitchen with a large island, bar stools, and a wine rack.

Anchored Inn at Hidden Harbour Marina

Deale

10/10 Excellent

We needed overnight accommodations before heading out for a day of sailing on the bay and Hidden Harbour popped up as the closest venue geographically and we're glad it did. The accommodations are new, with quality and fixtures and bathrooms that you wouldn't mind taking home with you. The price seemed fair and as we watched the full moon rising from our deck we wished that we were spending a week.

Rico

A modern lobby with a stone fireplace, a blue patterned rug, a blue sofa with colorful cushions, a brown leather chair, and a round coffee table.

Fairfield Inn & Suites by Marriott Easton

Easton

10/10 Excellent

The Fairfield Inn on US50 has become our go-to mid-range hotel in Easton. We have stayed here several times in recent years, and once again had a great experience during this Christmas stay. The facilities are clean and in good condition. The staff is friendly, welcoming, and accommodating. When I booked our stay this time through a third-party, I got a little confused about room options, and took the only king-bed room that I saw. The manager didnt know I had any concerns, and when the staff...

Richard

A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a large island with stools.

The Oaks Waterfront

Easton

10/10 Excellent

William

A lakeside view with sailboats, grassy areas, and white Adirondack chairs.

Sandaway Suites & Beach

Oxford

10/10 Excellent

joseph

Two Adirondack chairs facing a calm body of water with a clear sky above.

Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville

10/10 Excellent

The staff is friendly and helpful. The pool is refreshing, and I love the benches overlooking the waters and jetty from which you can view a lot of nature. There is always complimentary coffee and tea and apples available as well as filtered water. The best for me is that the property is on the Cross Island Trail so I can enjoy a walk/run or bike ride (you can rent bikes) to Terrapin Nature Park on the other side of Kent Island. It's also a short walk to a handful of great restaurants. We look...

Christina

A modern hotel dining area with a long table, four chairs, and three pendant lights.

Hampton Inn Easton

Easton

10/10 Excellent

Anonymous traveler

A spacious living room with a fireplace, a sofa, a coffee table, and a staircase leading to another level.

Best Western Plus Easton Inn & Suites

Easton

10/10 Excellent

Everything was good with checkin ,check out, and the room. The only complaint I can voice is with the breakfast service attendant. She was not very warm or inviting, did not speak to guest. She did have everything out and the area clean, but at the end of breakfast time, she removed all plates and bowls first so no one could get anything else to eat. We were late eating on our 3rd morning, but were in time to get our food before she started putting away. But then put chairs on the tables so...

Nancy

A large, stately house with a grand entrance, multiple windows, and a symmetrical facade.

The Tidewater Inn

Easton

10/10 Excellent

Maria

An indoor swimming pool with lounge chairs and a no diving sign.

Holiday Inn Express Easton by IHG

Easton

10/10 Excellent

Belinda

A two-story house with a swimming pool, outdoor seating, and a covered patio area.

George Brooks House B&B

St. Michaels

10/10 Excellent

Excellent B&B with a pool! the pool was clutch because we were there probably on the hottest days of the year so going in after a long day of walking around was nice. Used the pool until 10pm. Food was good, room was clean, people were nice. What else could you ask for. The only thing I noticed (and it wasn't a big deal) was the mirror in the room was too low on the wall (I'm 5'8 and still had to bend a little) and there was only one mirror so if you're in a hurry getting ready with your spouse...

Anonymous traveler

A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.

The Inn at Chesapeake Bay Beach Club

Stevensville

10/10 Excellent

Chuck

A large, two-story barn-style building with a covered front porch and a garage.

Kent Island Resort

Stevensville

10/10 Excellent

I stayed here for a quick overnight and did not utilize many of the amenities however, the staff was incredibly kind overall and with tips on dinner. This place is historic, which is a nice way of saying old but classic. Don’t expect a huge room, the photos portray the room accurately. Some things were a little rickety, but everything was clean. Overall I recommend this if you’re solo or a couple looking for a place as you enjoy the bay.

John

Find out more about Tilghman

Everything you need to know about Tilghman vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Tilghman vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Tilghman vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Tilghman vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Tilghman. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Tilghman in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $256 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Tilghman rentals

At Expedia, we put the best Tilghman vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Tilghman rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Tilghman vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Tilghman. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Are there vacation rentals in Tilghman?

Yes, you can find vacation rentals in Tilghman near Phillips Wharf Environmental Center, or you can go with a secluded option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals that Tilghman has to offer?

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach: Visitors like this Tilghman vacation home rental. It is located near the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals will I find in Tilghman?

Expedia has 16 vacation rentals for your stay in Tilghman.

What’s there to see and do in Tilghman?

Northern Chesapeake Bay and Chesapeake Bay are a couple of scenic spots to enjoy the outdoors, whereas Tilghman Watermen’s Museum is one of the cultural attractions. While here, Phillips Wharf Environmental Center and Tilghman Island Marina are other places worth a visit.

What’s a vacation rental in Tilghman like?

Vacation rentals are private properties you can book for a long or short time in Tilghman. Vacation rentals offer amenities like laundry facilities and kitchens so you'll have everything you want. If you're concerned about a clean environment, a vacation rental can provide a sense of safety away from shared hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental a popular option for a family trip or a small group gathering.

Tilghman Vacation Rentals

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Tilghman vacation rentals

1. Beachside Oasis with Beach Passes & King Suite by A Haven Away

2. The Cozy Crab- Your Charming Haven in Lovely North Beach!

3. WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

4. Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

5. Relax on Kent Island in 4 Bedroom Home w/Waterview

6. 2 bedroom waterfront property. Newly remodeled apartment with peaceful vibes.

7. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

8. Family Beach House: Spacious Deck, Grill & Views

9. 3-bedroom house in Deale located on Bay many amenities and great views

10. Plum Point Cottage #14

11. Charming Coastal/Country Home w/3 Acres & Sauna!

12. Plum Point Cottage #17

13. Plum Point Cottage #15

14. Cambridge Apt in Walkable Neighborhood

15. EASTON Beautiful APT. 3bed3bathKitchinDining/living room-walk to all places

16. Cass-N-Reel Luxury Houseboat

17. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

18. Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

19. Sunset Cottage - West River Access and Views!

20. Cambridge Apt in Walkable Neighborhood

Find vacation rentals that suit your style

Top Tilghman Hotel Reviews

Knapps Narrows Marina & Inn

10/10 Excellent

Find out more about Tilghman

Everything you need to know about Tilghman vacation rentals

Tilghman vacation rentals: An excellent choice for every season

How to find incredible deals on Tilghman rentals

Frequently Asked Questions

Are there vacation rentals in Tilghman?

What are some of the best vacation home rentals that Tilghman has to offer?

How many vacation rentals will I find in Tilghman?

What’s there to see and do in Tilghman?

What’s a vacation rental in Tilghman like?

Explore a world of travel with Expedia

3. WATERFRONT!! HOT TUB 3 bedroom Oasis on 2+ acres - Sleeps 8