A rocky shoreline with waves crashing onto the beach, a clear blue sky, and a forested area in the distance.

Tilghman Island Vacation Rentals

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Our top choices for Tilghman Island vacation rentals

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

Beachside Oasis with Beach Passes & King Suite by A Haven Away
North Beach
10.0 out of 10, Exceptional, (24 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is CA $137
CA $478 total
includes taxes & fees
Oct 19 - Oct 20
Beachside Oasis with Beach Passes & King Suite by A Haven Away

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

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (16 reviews)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
The price is CA $379
CA $768 total
includes taxes & fees
Oct 19 - Oct 20
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

3. Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (55 reviews)
"Our host Adam was wonderful and very communicative. We love the house and the location was just great. It was close to everything and had water views. We will certainly come back again."
United States
Rebecca B.
The price is CA $129
CA $415 total
includes taxes & fees
Oct 21 - Oct 22
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

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

The Cozy Crab- Your Charming Haven in Lovely North Beach!
North Beach
9.6 out of 10, Exceptional, (30 reviews)
"Wonderful place to visit "
United States
James L.
The price is CA $169
CA $408 total
includes taxes & fees
Oct 21 - Oct 22
The Cozy Crab- Your Charming Haven in Lovely North Beach!

5. Plum Point Cottage #14

Plum Point Cottage #14
Huntingtown
9.8 out of 10, Exceptional, (9 reviews)
"we had a great stay at this property for an impromptu weekend getaway. "
United States
Yonnick H.
The price is CA $464
CA $777 total
includes taxes & fees
Oct 20 - Oct 21
Plum Point Cottage #14

6. Cambridge Apt in Walkable Neighborhood

Cambridge Apt in Walkable Neighborhood
3.0 star property
Cambridge
10.0 out of 10, Exceptional, (1 review)
"This apt was built in the 50’s, or back when fewer outlets were needed, and it has window air conditioners. It was just what we were looking for as we visited the ste for family reunions"
United States
LOIS
The price is CA $135
CA $458 total
includes taxes & fees
Oct 23 - Oct 24
Cambridge Apt in Walkable Neighborhood

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

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
North Beach
10.0 out of 10, Exceptional, (40 reviews)
"This property and host were excellent. Property was as advertised. Lovely, clean, quiet and comfortable. Owner was super responsive and check in and check out was easy. 100% recommend."
United States
Sarah
The price is CA $217
CA $666 total
includes taxes & fees
Nov 9 - Nov 10
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

8. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (75 reviews)
"Just what was needed for our weekend stay."
United States
barbara s.
The price is CA $1,064
CA $1,875 total
includes taxes & fees
Oct 18 - Oct 19
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

9. Plum Point Cottage #15

Plum Point Cottage #15
Maryland
The price is CA $463
CA $821 total
includes taxes & fees
Oct 21 - Oct 22
Plum Point Cottage #15

10. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 reviews)
"Our family enjoyed staying at the Sunset Cottage. It was clean, had everything we needed for a great trip and the communion was amazing."
United States
Michelle H.
The price is CA $348
CA $718 total
includes taxes & fees
Nov 10 - Nov 11
Sunset Cottage - West River Access and Views!

11. Rose Haven Coastal Cottage

Rose Haven Coastal Cottage
North Beach
10.0 out of 10, Exceptional, (3 reviews)
"Warm and cozy- amazing home, beautiful area"
United States
Sodbileg
The price is CA $319
CA $618 total
includes taxes & fees
Oct 19 - Oct 20
Rose Haven Coastal Cottage

12. Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cambridge
9.4 out of 10, Exceptional, (26 reviews)
"Pet friendly!"
United States
Mary Beth S.
The price is CA $248
CA $560 total
includes taxes & fees
Nov 16 - Nov 17
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

13. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
9.6 out of 10, Exceptional, (19 reviews)
"The perfect off-season get-away! "
United States
Pamela B.
The price is CA $338
CA $764 total
includes taxes & fees
Oct 19 - Oct 20
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

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

Family Beach House: Spacious Deck, Grill & Views
Chesapeak beach
9.2 out of 10, Wonderful, (7 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is CA $204
CA $643 total
includes taxes & fees
Nov 2 - Nov 3
Family Beach House: Spacious Deck, Grill & Views

15. Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (40 reviews)
"Wonderful place to stay."
United States
Sharon D.
The price is CA $220
CA $361 total
includes taxes & fees
Oct 26 - Oct 27
Sailwinds Loft at Cambridge Creek

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (47 reviews)
"Great location, house was very clean, ample space and Adam was super communicative. Will definitely stay again!"
United States
Michelle P.
The price is CA $115
CA $399 total
includes taxes & fees
Oct 18 - Oct 19
Charming Coastal/Country Home w/3 Acres & Sauna!

17. Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (67 reviews)
"It was perfect for our overnight on way to NY!"
United States
Meagan G.
The price is CA $294
CA $357 total
includes taxes & fees
Oct 20 - Oct 21
Waterfront Getaway with Dock

18. 3-bedroom house in Deale located on Bay many amenities and great views

3-bedroom house in Deale located on Bay many amenities and great views
Deale
The price is CA $255
CA $625 total
includes taxes & fees
Oct 21 - Oct 22
3-bedroom house in Deale located on Bay many amenities and great views

19. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is CA $372
CA $640 total
includes taxes & fees
Oct 18 - Oct 19
Plum Point Cottage #17

20. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

3-bedroom house in soothing Saint Leonard with AC for relaxing stays
Saint Leonard
10.0 out of 10, Exceptional, (8 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is CA $166
CA $362 total
includes taxes & fees
Oct 26 - Oct 27
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Tilghman Island Hotel Reviews

Find out more about Tilghman Island

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Tilghman Island. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.