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Tilghman Holiday Rentals

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Holiday Rentals in Tilghman

Tilghman Waterfront | Indoor Pool | Private Dock | Pool House

9.4 out of 10, Exceptional, (6)
"The home was beautiful, the indoor pool was great Everything about the home was perfect for our family vacation (4generations). The only thing that was not enjoyable was the flooding caused by hurricane Debby but it did leave us with memories. . Eastern Shores is a great host and kept us informed "
Tilghman Waterfront | Indoor Pool | Private Dock | Pool House

Relaxing Waterfront Cottage Near St Michaels, Maryland

9.8 out of 10, Exceptional, (217)
"Were pleased with the property and surroundings. Very beautiful, ancient trees. Neighborhood was quiet and the river and dock were favorite reading spots. Enjoyed!!!"
Relaxing Waterfront Cottage Near St Michaels, Maryland

Charming Annapolis WaterVIEW Home

9.6 out of 10, Exceptional, (49)
"Wonderful location to downtown Annapolis! Beautiful home, well maintained and plenty of room. The porch overlooking the bay has a table for 10 which provided a wonderful setting for our family. This is our second stay and we’ll absolutely stay again "
Charming Annapolis WaterVIEW Home

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (47)
"Everything close by!"
The Blue Crab Beach House - Free beach passes

Walk to Everything House

10.0 out of 10, Exceptional, (72)
"We thoroughly enjoyed the convenience of walking to shops, restaurants, and waterfront! Residence was charming and clean! Only minor issue was we couldn’t locate the iron- just the ironing board! We still had fun but we’re just a bit wrinkled!😁"
Walk to Everything House

Private Waterfront Woods | Dock, Kayaks, Views

10.0 out of 10, Exceptional, (14)
"Enjoyed the location and proximity to the city. Water view and firepit enjoyable. Disappointed that the dock and kayaks not easily accessible. House needs some tlc (we provided a list of easy repairs/maintenance needed.) Love to know why the ceiling fans and lights go on and off randomly."
Private Waterfront Woods | Dock, Kayaks, Views

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

9.6 out of 10, Exceptional, (17)
" October 11-14, 2024, we rented the “Willoughby” for a family reunion. Let me start out by saying this home is amazing. It looks exactly as pictured based on the website photos. It was even better than I expected. If you are considering this property, I highly recommend booking it! Believe me when I say the Willoughby is a rare gem. The location of the home is perfect and extremely private. The grounds are pristine and the view of the water is breathtaking. The home sits on the Hudson...
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

9.8 out of 10, Exceptional, (35)
"The groomsmen and their families attending my daughter's nearby wedding stayed at this spectacular property. I heard nothing but high praise for its beauty, amenities, and comfort. So glad this all worked out for the dates we needed it for!"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (30)
"Excellent experience."
The price is AU$417
includes taxes & fees
2 Dec - 3 Dec
Relax on Kent Island in 3 Bedroom Home w/Waterview

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

9.8 out of 10, Exceptional, (32)
"Four of my friends and I stayed at this cute home for a ladies' weekend (two nights) in St. Michaels. We are in our early 40's and all agreed that the location of this home is superb. We walked to dinner each night (Limoncello and Ruse, both great) and enjoyed the wonderful shops in the lovely downtown area. The location of this home cannot be beat if you want to park your car upon arrival and not have a need to use it again during your stay. We had three cars, two of which fit in the driveway...
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Cass-Away Luxury Houseboat

10.0 out of 10, Exceptional, (87)
"All as advertised Wonderful option to a hotel"
Cass-Away Luxury Houseboat

Your Annapolis Adventure Starts Here!!

10.0 out of 10, Exceptional, (136)
"My family and I love staying here! It's clean, beautiful, spacious, and comfortable. It's home away from home. I love all the special touches--lots of cozy blankets, the beautiful decor, the comfortable beds. And, of course, it's close to anything you want to do in Annapolis or the surrounding areas. During this stay, we were able to enjoy the patio, which was especially wonderful to be able to do in November. My favorite spot is the sitting area next to the kitchen; it's a perfect place to...
Your Annapolis Adventure Starts Here!!

Pool and Bay Views on wrap around deck in Kent Island

9.6 out of 10, Exceptional, (24)
"We loved everything about the Kent Island House! Would book again in a hot minute"
Pool and Bay Views on wrap around deck in Kent Island

The Lazy Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (38)
"The Lazy Crab was such a delightful home to visit. The kitchen was fully stocked and the house had everything any traveler could need, including a washer and dryer! It was evident that the owners put a lot of love into making sure guests enjoyed their stay. I highly recommend! You will feel right at home."
The Lazy Crab Beach House - Free beach passes

Mid-Century Modern and Marvelous on the Bay

10.0 out of 10, Exceptional, (70)
"The house was amazing! From the moment the front door opened it was a visual feast. The views are incredible, it's quiet, private and very relaxing. There were personal elements reflecting the current and original owners which we found very interesting and the attention to detail throughout was superb! Everything was incredibly well stocked with a multitude of extras. "
Mid-Century Modern and Marvelous on the Bay

Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

10.0 out of 10, Exceptional, (204)
"Very cozy and clean. Beautiful surroundings with direct view of the water. "
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

Charming Cottage with Hot Tub 1 Block from the Bay

10.0 out of 10, Exceptional, (8)
"Very clean - well equipped - perfect for our relaxing weekend."
The price is AU$902
includes taxes & fees
3 Dec - 4 Dec
Charming Cottage with Hot Tub 1 Block from the Bay

Bay View Studio Apartment

10.0 out of 10, Exceptional, (39)
"Right on the water. Very quiet, spacious and nice. Host was on top of things. "
Bay View Studio Apartment

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

9.8 out of 10, Exceptional, (168)
"We went to St. Michael’s for a wedding. The cottage was great. Very charming. The location was perfect. We could walk everywhere. We had great communication with the host. He was very accommodating. We will stay there again. "
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Cass-N-Reel Luxury Houseboat

10.0 out of 10, Exceptional, (17)
"Very relaxing"
Cass-N-Reel Luxury Houseboat
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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Other types of properties in Tilghman you may be interested in

The Tilghman Island Inn

3.5 star property
9.8 out of 10, Exceptional, (77)
"Loved our secluded it was and right in the water. Very peaceful. "
The price is AU$347
includes taxes & fees
1 Dec - 2 Dec
The Tilghman Island Inn

Knapps Narrows Marina & Inn

3.0 star property
9.4 out of 10, Exceptional, (319)
"Amazing place to stay "
The price is AU$203
includes taxes & fees
1 Dec - 2 Dec
Knapps Narrows Marina & Inn

Hyatt Regency Chesapeake Bay

4.0 star property
8.8 out of 10, Excellent, (1049)
"Anniversary. Great time. Beautiful property "
The price is AU$369
includes taxes & fees
2 Dec - 3 Dec
Hyatt Regency Chesapeake Bay
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Are there holiday rentals in Tilghman?

Yes, there are holiday rentals in Tilghman close to Phillips Wharf Environmental Center, or you can select a more secluded option if you're looking for a relaxing stay.

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

Charming Annapolis WaterVIEW Home: This holiday home rental outside of Tilghman is located on the waterfront, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

How many holiday rentals will I find in Tilghman?

Expedia has 20 holiday rentals for your stay in Tilghman.

What’s there to see and do in Tilghman?

Cultural attractions include Tilghman Watermen’s Museum, whereas Phillips Wharf Environmental Center is just one of the family-friendly sights. St. Michaels Winery and Chesapeake Bay Maritime Museum are a couple of places you'll find in the wider area.

What’s a holiday rental in Tilghman like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Tilghman. Holiday rentals offer extras such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from shared hotel lifts and busy front desks while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive option for a family getaway.