Photo by Kacy Kish

Search Holiday Rentals in Tilghman

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Top Holiday Rentals in Tilghman

The Blue Crab Beach House - Free beach passes
Beach nearby, sun-loungers, beach umbrellas, beach towels
The Blue Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, (37)
"This property is in a great location! The house is adorable and the owner was very responsive and accommodating when I needed to add an extra day. I would definitely recommend!"
The Blue Crab Beach House - Free beach passes
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Exterior
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, (186)
"The cottage is fully stocked, clean, and cozy. We thoroughly enjoyed sitting on the deck and watching all the wildlife."
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Charming Cottage with Hot Tub 1 Block from the Bay
Property grounds
Charming Cottage with Hot Tub 1 Block from the Bay
10.0 out of 10, Exceptional, (6)
"had a wonderful time We haven’t done this family get away in a long time and it was such a great and memorable experience for us, our kids and grandkids. Hope in the summer we get the opportunity to reserve your place again. Thank you!"
The price is £439
includes taxes & fees
6 May - 7 May
Charming Cottage with Hot Tub 1 Block from the Bay
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Property grounds
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
10.0 out of 10, Exceptional, (22)
"My family and I had an amazing stay!! Jacob’s correspondence was timely and very friendly from beginning to end. We had some problems with cleanliness (sheets not being washed, cobwebs, dead beetles in windowsills), and Jacob refunded our cleaning fee. Despite that, the house was beautiful and had plenty of space for our big family to move around. Be warned that there are A LOT of stairs! But nothing my older parents couldn’t handle. The views are absolutely breathtaking and every single room...
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
10.0 out of 10, Exceptional, (72)
"The house has a beautiful view of the water. Being so close to the Happy Harbor restaurant, we could order carryout & listen to the bands from the screened-in porch. It was a perfect getaway for someone who had relaxation on the mind. Thanks for sharing your lovely home."
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Bay View Studio Apartment
Outdoor spa tub
Bay View Studio Apartment
10.0 out of 10, Exceptional, (25)
"If you are looking for a very spacious well-appointed one bedroom apt. style accommodation in a residential setting with lovely waterfront bay views, I highly recommend this place!"
Bay View Studio Apartment
Maryland Vacation Rental w/ Private Pool & Dock
Property grounds
Maryland Vacation Rental w/ Private Pool & Dock
10.0 out of 10, Exceptional, (3)
"Loved the house and kids loved the pool. We also managed to catch a half dozen crabs (August trip). House is on the smaller side, but with four bedrooms everyone had privacy and just what they needed. We'll be back!"
Maryland Vacation Rental w/ Private Pool & Dock
Stunning Waterfront Maryland Eastern Shore Home with In-Ground Pool and Hot Tub
Fridge, microwave, oven, stovetop
Stunning Waterfront Maryland Eastern Shore Home with In-Ground Pool and Hot Tub
10.0 out of 10, Exceptional, (30)
"Great place to recharge for a few days as a family! Beautiful and peaceful in the fall — though my kids are ready to come back and use the pool in warmer weather!!!"
Stunning Waterfront Maryland Eastern Shore Home with In-Ground Pool and Hot Tub
7 mins away from Downtown Annapolis
Property grounds
7 mins away from Downtown Annapolis
10.0 out of 10, Exceptional, (5)
"The home was very clean and beautifully set up. The property managers were very helpful and communicative. they even had complimentary snack, beverages, and even a hand written note with a wine bottle. Bathrooms were clean and stocked with everything incase you forgot something at home. Everyone enjoyed the home, we were planning our next visit before we even left!"
7 mins away from Downtown Annapolis
The Lazy Crab Beach House - Free beach passes
Property grounds
The Lazy Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, (22)
"Nice neighborhood! Easy walkable area to restaurants and the beach."
The Lazy Crab Beach House - Free beach passes
Great location, free parking
Fridge, microwave, oven, stovetop
Great location, free parking
10.0 out of 10, Exceptional, (24)
"The house is in a great location near the water and close to downtown Annapolis. The house itself was perfect for our group and had everything we needed. The owner, Gibson, was very helpful and communicative and if this house was ever available again would definitely stay there."
Great location, free parking
Circa 1700 Chesapeake Colonial home on the National Register.
Exterior
Circa 1700 Chesapeake Colonial home on the National Register.
10.0 out of 10, Exceptional, (41)
"This is a beautifully restored getaway that was right across from a bike trail. They also had a canoe and kayaks available with a dock to launch. Annapolis is only 20 minutes away and the owners were so kind and helpful. We thoroughly enjoyed ourselves here."
Circa 1700 Chesapeake Colonial home on the National Register.
Charming Annapolis WaterVIEW Home
Property grounds
Charming Annapolis WaterVIEW Home
9.8 out of 10, Exceptional, (41)
"We were friends gathering for a visit to relax and catch up and the house was perfect for that! It was very comfortable, in a quiet neighborhood, but close to enjoy going to local restaurants and shopping. We loved the large windows that looked out over the Bay! The decor was unique interesting touches."
The price is £551
includes taxes & fees
8 May - 9 May
Charming Annapolis WaterVIEW Home
Relax on Kent Island in 3 Bedroom Home w/Waterview
Exterior
Relax on Kent Island in 3 Bedroom Home w/Waterview
9.8 out of 10, Exceptional, (19)
"We have nothing but great things to say about Adam and his beautiful home! He was so accommodating and the home was comfortable and spacious for our family of 5! Couldn’t have had a better experience :)"
The price is £205
includes taxes & fees
7 May - 8 May
Relax on Kent Island in 3 Bedroom Home w/Waterview
Relaxing Waterfront Cottage Near St Michaels, Maryland
Exterior
Relaxing Waterfront Cottage Near St Michaels, Maryland
9.8 out of 10, Exceptional, (194)
"Lovely setting, comfy home. Planning on staying there again."
Relaxing Waterfront Cottage Near St Michaels, Maryland
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
3 bedrooms, desk, iron/ironing board, free WiFi
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
9.8 out of 10, Exceptional, (100)
"Really enjoyed our time there. Very relaxing. Comfortable home. All amenities there. Especially loved the windows..."
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Fridge, microwave, oven, stovetop
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, (25)
"My family and I enjoyed our stay at the Carpenter Alley Cottage in Saint Michaels! The location was perfect -- walking distance from everything! Appreciated that there was a ground floor bedroom for my parents so they didn't have to climb the stairs and my daughter loved having her own bunk bed room! I did have a few questions about the cottage and the check-in process and my inquiries were all met with a prompt response. Would love to stay here again! (One note though is that it is a smaller,...
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Pool and Bay Views on wrap around deck in Kent Island
Outdoor pool
Pool and Bay Views on wrap around deck in Kent Island
9.6 out of 10, Exceptional, (21)
"Everyone really loved the house and the location. The pool was great"
Pool and Bay Views on wrap around deck in Kent Island
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Fridge, microwave, stovetop, dishwasher
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
9.6 out of 10, Exceptional, (4)
"We extremely enjoyed our stay. The house was beautiful, kitchen was well equipped and the view was spectacular, especially with the Eagles that have nested on the 32 acre property. However was disappointed in the fact that the fire places were not in working conditions and rooms should have been number. We enjoy kayaking up and down the bay and taking it all in. I would definitely stay again."
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
Fridge, microwave, oven, stovetop
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
9.6 out of 10, Exceptional, (98)
"We were in town for the weekend and wanted to stay in the same neighborhood where we have had our summer vacation for years. This time, we had our dog with us. There was far more space than we needed, but it's making us think we might want to come back with friends or family. The large yard was perfect for the dog, and we loved being able to sit on the large front porch and to walk to our favorite places in Eastport so easily. Easy access to the house and parking--and Oscar's coffee...
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
Don't see what you're looking for?
See all available properties in Tilghman
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.

Other types of properties in Tilghman you may be interested in

The Tilghman Island Inn
Garden View Double Queen First Level - Not Dog Friendly | View from room
The Tilghman Island Inn
3.5 star property
9.8 out of 10, Exceptional, (48)
"This hotel/inn was perfect. Our stay was amazing. I proposed to my now fiancé and the hotel helped me plan and helped with the room to celebrate. The staff is super sweet and very hospitable. We had a lovely time and will come back in the near future!"
The price is £233
includes taxes & fees
23 May - 24 May
The Tilghman Island Inn
Knapps Narrows Marina & Inn
Exterior
Knapps Narrows Marina & Inn
3.0 star property
9.4 out of 10, Exceptional, (302)
"Super friendly staff at check in. Gorgeous view. Great stay. "
The price is £184
includes taxes & fees
4 May - 5 May
Knapps Narrows Marina & Inn
Hyatt Regency Chesapeake Bay
Indoor pool, 2 outdoor pools, pool umbrellas, pool loungers
Hyatt Regency Chesapeake Bay
4.0 star property
8.8 out of 10, Excellent, (1002)
"This was our 6 time visiting the resort. We love everything about the place. The only concern we have is the parking. We have 2 sons with Down Syndrome, so it would be nice if there was handica parking a little closer to the hotel."
The price is £176
includes taxes & fees
22 May - 23 May
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.

Everything you need to know about Tilghman holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Tilghman holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Tilghman holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Tilghman holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Tilghman holiday rentals we have selected for you start as low as £205 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Tilghman rentals

At Expedia, we put the best Tilghman holiday 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 holiday.

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 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?

The Blue Crab Beach House - Free beach passes : This holiday home rental outside of Tilghman is located near the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Kick off your shoes and enjoy yourself with a private garden and a selection of games.

How many holiday rentals will I find in Tilghman?

Expedia has 17 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.

Recent reviews of Tilghman properties
Expedia verified reviews

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

5/5 Excellent
"This was our 6 time visiting the resort. We love everything about the place. The only concern we have is the parking. We have 2 sons with Down Syndrome, so it would be nice if there was handica parking a little closer to the hotel."
A verified traveller stayed at Hyatt Regency Chesapeake Bay
Posted 16 hours ago
Hyatt Regency Chesapeake Bay