Discover a selection of 293 vacation rentals in Tilghman, MD that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $250 per night, and houses and cottages are popular options for a stay in Tilghman. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Tilghman
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Destination guide

The waterfront setting of Tilghman is ready to explore

The island views and wildlife provide a pleasant backdrop to your vacation home in Tilghman. This city's fishing, bird watching and boating draw many visitors. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Things to do

Sightseeing in and around Tilghman

Are you hoping to discover attractions to visit in the city? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Tilghman a one-of-a-kind vacation spot. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • St. Michaels Winery (8.2 mi / 13.3 km)
  • Chesapeake Beach Water Park (10.7 mi / 17.2 km)
  • Phillips Wharf Environmental Center (1 mi / 1.6 km)
  • Talbot Massage (15.7 mi / 25.2 km)
  • Easton Cycle and Sport (15.7 mi / 25.3 km)
Natural features

Exploring the natural landscape of Tilghman

Travelers enjoy Tilghman for its island views and sunsets. Whether you're an adventurous traveler or just want to take in the scenery, Tilghman is a great place to get outside. These are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city center:

  • Breezy Point Beach (11.1 mi / 17.9 km)
  • Great Marsh Park (16.3 mi / 26.2 km)
  • Blackwater National Wildlife Refuge (22.5 mi / 36.2 km)
  • Triton Beach (14.9 mi / 24 km)
  • Franklin Point State Park (12.1 mi / 19.5 km)
  • Shadyside Park (13.7 mi / 22.1 km)
How to get there

Transportation to and around Tilghman

Fly into Baltimore Washington Intl. Airport (BWI), the closest airport, located 37.4 mi (60.1 km) from the city center. If you can't find a flight that works for your travel itinerary, you can also fly into Easton, MD (ESN-Easton - Newnam), which is 16.5 mi (26.6 km) away.

What are the top vacation rentals in or near Tilghman?

Whether you're looking for an intimate retreat for you and your special someone or somewhere spacious to fit the family, you'll find some top vacation rentals in and around Tilghman. Here are a couple to get you started:

  • Around 20 miles from the center of Tilghman, it's hard to top "Brand New Renovation In Historic District With 2 Parking Spots". It has 2 bedrooms and a host of amenities including a free nearby fitness center and a stovetop.
  • Another great option is "Water Front Retreat - Sunrise And Sunset Water Views", which is around 30 miles from Tilghman. Offering 3 bedrooms, a stovetop and cable/satellite TV services, it has everything you need to keep you comfortable and content.

For even more great options, use the search bar at the top of the page to find the perfect Tilghman vacation rental for you.

What are the best tiny house vacation rentals in or near Tilghman?

Punching above its weight when it comes to character and ingenuity, a tiny house vacation rental in Tilghman promises big adventure. Close down your tech and switch your focus to Mother Nature at one of these pocket-sized escapes:

  • Look forward to a simpler way of life at "Annapolis Waterfront "tiny House" In Garden Setting". Amenities at this small wonder in Parole include a hair dryer and air conditioning.
  • "A Serene Tiny Home Experience" offers conveniences such as golf and a hair dryer. Located in Parole, you'll be able to live big in this small but nicely designed property.

What are the top-rated vacation rentals for weekend getaways in or near Tilghman?

At Vrbo, we think weekends were made for fun. Stay in one of these weekend getaways in and around Tilghman and take advantage of all the wonderful things to do close by:

  • "Peaceful Cambridge Home On Jenkins Creek" is a favorite option around 15 miles southeast of central Tilghman. There's no need to go far to find something to do around here. Pull out your map and head for Queenstown Harbor Golf Club and Long Wharf Park. Activities like tennis and fishing will add the perfect finishing touch to your quick break.
  • "Charming Historic Home Just Steps From Main Street" is another great property where you can escape the everyday. Around 20 miles northwest of Tilghman, use it as a base to try some cycling or fishing. Carrs Beach and Carroll Park also have to be on your itinerary while you're here.

Can I find studio apartments for rent in and around Tilghman?

Take in the energy and culture of Tilghman from the comfort of your own studio apartment. Whether you're planning to take time out on your own or paint the town red with pals, we'll help you find the perfect studio apartment for rent in or near Tilghman:

  • Explore the world around you and then sleep soundly at "Annapolis Waterfront "tiny House" In Garden Setting". This property is a terrific base for discovering the sights and offers amenities including air conditioning and a kitchen.
  • "Beautiful Condo - Water View Near City Dock" is another fabulous choice. Make yourself comfy and take advantage of a smart TV, golf and more.

With the money you save on your studio apartment, you'll be able to discover even more of Tilghman. Cultural sights like Bruce Gabrielson's Surf Art Gallery and Museum and OXOXO Gallery will help you get a feel for the personality of this destination.

Can I find short term rentals in or near Tilghman?

Short-term rentals are in good supply in and around Tilghman. Chill out for the weekend in an upmarket bed & breakfast, a cozy cottage or a spacious house. Whatever type of vacation rental you'd like, you'll have plenty to select from with Vrbo. Here are a few of our favorites:

  • "Charming Historic Home Just Steps From Main Street" is near the center of Tilghman, so you'll have loads of things to keep you entertained. Visit notable sights like Annapolis Bowl and Eisenhower Golf Course when you're not kicking back in your cozy property.
  • Wake up, make a cup of coffee and then plan what to explore around "Gorgeous Annapolis Getaway - Walk Everywhere". Walden Golf Club and Crofton Bowl should be on your itinerary if you stay at this popular rental.

What are the best romantic weekend getaways in or near Tilghman?

Forget flowers and chocolates. Sometimes all you need is to take off for the weekend, just you and your beloved. At Vrbo, we've got romantic getaways in and around Tilghman that would make Cupid green with envy. Here are some we think you'll be enamored with:

  • Put on some relaxing tunes and chill together at "Brand New Renovation In Historic District With 2 Parking Spots". Around 20 miles from Tilghman, this property has everything you need for a couple's weekend away, including a fireplace and beauty services.
  • "Water Front Retreat - Sunrise And Sunset Water Views" is another terrific option that'll woo you. It's around 30 miles from Tilghman and comes with beauty services and a fireplace.

What are the best large group vacation rentals in or near Tilghman?

Check out these large group vacation rentals in or near Tilghman and don't worry about leaving anyone off your invite list:

  • A nice range of amenities including a garden and a kitchen make "Ultraclean Waterfront Home Annapolis Area" a favorite. This sprawling property has 5 bedrooms and accommodates up to 12 people. From the center of Tilghman, it's around 30 miles away to the north.
  • "240' Private Beachfront @kent Island Love Point" is another fantastic option. It's around 25 miles to the north of Tilghman, has 5 bedrooms and welcomes up to 26 guests. A water park and a firepit are among the things designed to make your stay even more memorable.

What are the best houses for rent with a pool in or near Tilghman?

A pool is often a must-have when choosing where to stay, especially if you've got kids in tow. Check out these houses with a pool in or near Tilghman and spend your days splashing around:

  • Treat the gang to a memorable stay at "Annapolis Waterfront "tiny House" In Garden Setting". There's plenty to love about this getaway apart from its pool, such as a living room and a garden.
  • Otherwise, recharge your batteries at "Premier St. Michaels Cottage - T. Blades House". Along with an invigorating pool, you can also make use of a barbecue grill and a fridge.

Tilghman has a humid subtropical climate, with average summertime temperatures ranging between 70 ºF and 80 ºF. But you don't have to wait until summer to visit. Check out the search bar at the top of the page and adjust the filters to find the ideal Tilghman vacation rental and organize your getaway for whenever you like.

What are the best large family vacation rentals in or near Tilghman?

Whether your ideal getaway is high in the mountains or down by the beach, you'll enjoy it even more if you share it with your favorite people. Consider one of these large family vacation rentals in or near Tilghman and bring along the whole crew:

  • Sleeping as many as 8 guests in 3 bedrooms, "Water Front Retreat - Sunrise And Sunset Water Views" is the perfect place to vacation with the family. This popular escape is 30 miles to the north of Tilghman and has creature comforts that include a kitchen island and on-site watersports.
  • "Charming Historic Home Just Steps From Main Street" is also popular with families. It's around 20 miles to the northwest of Tilghman, has 3 bedrooms and accommodates up to 8 guests. Handy amenities here include pet-friendly facilities and on-site watersports.

When you want to explore, there are plenty of family-friendly attractions in the area to keep everyone entertained. National Aquarium in Baltimore, Six Flags America and Maryland Zoo should be top of your must-do list.

Can I find family cabin rentals in or near Tilghman?

Escape from everyday life and treat the people you love to a different type of vacation. Stay in one of these family cabin rentals in or near Tilghman and get the camping experience — but with all the creature comforts!

  • "Stunning Views From Waterfront Log Cabin With Fireplace On The Chesapeake Bay" - This popular escape offers a toaster and a dining table and is located about 16 miles to the southwest of the center of Tilghman.
  • "Waterfront Cabin" - Round up the troops and spend a few days or more at this appealing stay, which is around 25 miles to the southwest of Tilghman. You'll have access to a barbecue grill, towels and a whole lot more.

For more options, use the search bar at the top of the page and adjust the filters to find the Tilghman vacation rental that's perfect for your needs.