Trappe vacation rentals

We found 140 vacation rentals — enter your dates for availability

Nestled in the heart of Maryland’s Eastern Shore, Trappe invites travelers to immerse themselves in its stunning landscapes and rich cultural heritage. With outdoor adventures along Marsh Creek Road, charming local museums, and scenic parks, this idyllic destination is perfect for families and groups seeking both excitement and relaxation. Whether you prefer cozy cottages or spacious vacation homes, Trappe’s accommodations provide the comfort and convenience of home, ensuring a memorable getaway for everyone.

Holiday rentals with weekly discounts - Trappe

Showing deals for:Dec 4 - Dec 11

Dining table- seats 10!
Pool
View from Foyer into Great Room
screened porch
Exceptional
(145 reviews)

Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks

Easton

9% off
$1,058
$7,404 for 7 nights
All fees included
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
Dining
Interior
Exterior
Interior
Very Good
(5 reviews)

Spacious waterfront house in charming Royal Oak with WiFi, AC, dock

Royal Oak

9% off
$1,251
$8,756 for 7 nights
All fees included
Spacious waterfront house in charming Royal Oak with WiFi, AC, dock
Interior
Private kitchen
Dining
Property grounds
Exceptional
(7 reviews)

Arcadia Shores on the Cove.

Easton

8% off
$610
$4,267 for 7 nights
All fees included
Arcadia Shores on the Cove.
Living area
Property grounds
Private kitchen
Room
Exceptional
(31 reviews)

A Luxury Home located in Easton with Water VIEWS! Close to Oxford/St. Michaels

Easton

9% off
$374
$2,616 for 7 nights
All fees included
A Luxury Home located in Easton with Water VIEWS! Close to Oxford/St. Michaels
Room
Private kitchen
Property grounds
Interior
Exceptional
(10 reviews)

3-bedroom waterfront retreat in Secretary, Maryland

Secretary

8% off
$471
$3,294 for 7 nights
All fees included
3-bedroom waterfront retreat in Secretary, Maryland
Property grounds
Outdoor dining
Living area
Dining
Exceptional
(13 reviews)

High Water Guest House<br>

Cambridge

9% off
$372
$2,605 for 7 nights
All fees included
High Water Guest House<br>
Living area
Marina
Dining
Private kitchen
Exceptional
(5 reviews)

New, Intown Waterfront Townhome wPool & Location!

Cambridge

9% off
$296
$2,070 for 7 nights
All fees included
New, Intown Waterfront Townhome wPool & Location!
Private kitchen
The beautiful marina is just 4 blocks away
Interior
Marina
Exceptional
(11 reviews)

Station House East: Upscale Loft in the Historic District Cambridge, MD

Cambridge

7% off
$127
$891 for 7 nights
All fees included
Station House East: Upscale Loft in the Historic District Cambridge, MD
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Find out more about Trappe

Why visit Trappe

  • Outdoor Activities: Trappe is perfect for nature lovers, offering plenty of parks and outdoor adventures.
  • Family-Friendly Excursions: Enjoy a range of activities suitable for families, ensuring an enjoyable experience for all ages.
  • Rich Heritage: Discover Trappe’s historical significance and romantic atmosphere through local museums and landmarks.
  • Charming Neighborhoods: Explore tranquil neighborhoods with picturesque homes and ample green spaces.
  • Variety of Accommodations: Choose from cozy homes, charming cottages, and comfortable apartments to suit your needs.

Popular types of accommodation in Trappe

If you're searching for the perfect getaway in Trappe, MD, you're in the right place. Our most popular types of vacation rentals include cozy houses, charming cottages, and comfortable apartments. Explore available rentals with photos to find the ideal space for your stay. Whether you're looking for an apartment in Trappe or a house for rent in MD, we have options that cater to every traveler's needs.

  • Houses: The top choice for visitors in Trappe, offering spacious and comfortable settings for families, friends, or couples.
  • Cottages: A charming option that provides a cozy and picturesque retreat for a more intimate stay.
  • Apartments: A practical choice for travelers seeking convenience and modern amenities in a central location.
  • House Boats: A unique lodging experience, perfect for those looking to enjoy waterfront views and a laid-back atmosphere.
  • Villas: Luxurious accommodations that offer extra space, upscale features, and beautiful surroundings.**

Top attractions near Trappe

Trappe, Maryland, is an ideal destination for outdoor enthusiasts and families seeking adventure. The area boasts a variety of attractions, including urban parks and history museums, offering cultural and outdoor experiences. Whether you’re traveling solo, with family, or friends, Trappe provides numerous opportunities to explore its rich heritage and natural beauty, making it a perfect spot for your vacation.

  • Choptank River Lighthouse: Situated 6 miles from Trappe, this historic lighthouse offers a glimpse into maritime history with its charming architecture and scenic views of the Choptank River, perfect for photography enthusiasts.
  • Gerry Boyle Park at Great Marsh: Located 5 miles away, this urban park is a family-friendly destination featuring walking trails, picnic areas, and beautiful marshland, ideal for outdoor activities and city vibes.
  • Harriet Tubman Museum and Educational Center: Also 6 miles from Trappe, this museum celebrates the life of Harriet Tubman, offering insightful exhibits that highlight her legacy and contributions to freedom and civil rights.

Things to do recommended for couples

For a romantic getaway in Trappe, indulge in a wine tasting at St. Michaels Winery, only 12 miles away, or relax with a soothing treatment at Talbot Massage, 8 miles from town. Don't miss the enchanting Layton's Chance Vineyard and Winery, located 14 miles away, for a delightful experience.

Things to do recommended for families

Families visiting Trappe, Maryland, can explore the scenic landscapes at the nearby Blackwater National Wildlife Refuge, perfect for birdwatching and hiking. Enjoy a fun day at the local parks or visit the charming shops in nearby Easton for a delightful family experience.

Things to do recommended for groups

Groups visiting Trappe can enjoy a captivating show at the Avalon Theatre, shop at Saint Michaels Village, or rent bikes at Easton Cycle and Sport for an adventurous day exploring the picturesque surroundings. Each activity promises a memorable experience infused with local charm.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Trappe

When planning your trip—whether you’re traveling with a group, enjoying a family getaway, bringing your pets along, or seeking extended stays—be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Trappe with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Trappe with young kids: Traveling with little ones can be quite a task. It's important to prioritize their comfort and safety, including having access to family-friendly amenities like a private pool. Additionally, think about how close you'll be to attractions that cater to families.
  • Taking your pets with you to Trappe: For many families, a trip isn’t truly fulfilling without their furry companion by their side. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Trappe: If you're searching for vacation rentals that offer deals for stays of a month or more, you've come to the right spot. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Trappe

Trappe, Maryland, is the perfect gateway for outdoor adventures and family-friendly excursions. Explore nearby neighborhoods that boast tranquil locations and charming family homes. Enjoy easy living with ample dog parks for your furry friends. Don't miss the chance to experience the rich history and romantic atmosphere that Trappe and its surroundings offer, making it an ideal destination for those seeking a memorable vacation.

  • St. Michaels: Located 13 miles from Trappe, St. Michaels is a charming waterfront town known for its picturesque views and outdoor activities. A perfect spot for romantic getaways and family vacations, visitors can stroll along the scenic boardwalk or explore the recreational areas that line the shore. Highlights include sandy beaches and tranquil lakes, where families can enjoy swimming, picnicking, or simply soaking up the sun. Don’t miss the local shops and eateries that offer fresh seafood and unique local crafts.
  • Cambridge: Just 6 miles away from Trappe, Cambridge invites adventure seekers and families alike to experience its vibrant boardwalk and recreational areas. Known for its friendly atmosphere, the city is a hub for outdoor activities, including fishing and kayaking along the Choptank River. Visitors can explore the shopping center for local boutiques and dining options, while the nearby esplanade provides a picturesque setting for leisurely walks. Don’t forget to check out the beautiful beaches that make Cambridge a favorite destination for families.
  • Easton: Situated 8 miles from Trappe, Easton is a delightful city that offers a blend of outdoor fun and family-friendly attractions. Known for its charming shopping center and vibrant mall, Easton is perfect for those looking to indulge in retail therapy. Families can enjoy the local beaches or visit historical monuments that tell the story of the area's rich heritage. The romantic ambiance makes it a great place for couples to explore quaint shops, dine at cozy restaurants, and enjoy the natural beauty surrounding the city.

Best time to go to Trappe

If you're planning a trip to Trappe, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in June to July and September, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January35.8°F (2.1°C)Light RainMostly SunnyAverageSlightly Low
February38.5°F (3.6°C)Light RainMostly SunnyAverageSlightly Low
March44.8°F (7.1°C)Light RainMostly SunnyAverageSlightly Low
April55.0°F (12.8°C)Light RainMostly SunnyAverageAverage
May64.0°F (17.8°C)Light RainMostly SunnyAverageAverage
June72.9°F (22.7°C)Light RainMostly SunnySlightly HighSlightly High
July78.1°F (25.6°C)Light RainMostly SunnySlightly HighSlightly High
August76.3°F (24.6°C)Light RainMostly SunnyAverageSlightly High
September70.5°F (21.4°C)Light RainMostly SunnySlightly HighAverage
October60.6°F (15.9°C)Light RainMostly SunnySlightly LowAverage
November48.9°F (9.4°C)Light RainMostly SunnySlightly LowAverage
December41.5°F (5.3°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is a breeze

Are you eager to save on your upcoming travel plans? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, consider booking a longer stay to unlock even greater savings. To discover a Vrbo property that aligns with your budget, simply use our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect spot for your getaway.

Vrbo Trips: Planning made easy

The Vrbo Trip Board offers a user-friendly platform to help you plan your travel. You can easily start new trips, resume planning from where you last stopped, or organize your existing itineraries. Your saved or booked properties are conveniently sorted into categories like Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Delight in the waterfront landscape of Trappe

The parks and other outdoor surroundings create an inviting atmosphere in Trappe. Renowned for its fishing, snowshoeing and boating, this city welcomes all 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.

Sightseeing in and around Trappe

Do you want to find attractions to see while you're in town? Venture out of your vacation home and check out everything that makes Trappe a one-of-a-kind vacation spot. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

  • St. Michaels Winery (12.3 mi / 19.7 km)
  • Hog Neck Golf Course (11.5 mi / 18.5 km)
  • Layton's Chance Vineyard and Winery (14.2 mi / 22.8 km)
  • Bay Country Shop (7 mi / 11.3 km)
  • Talbot Massage (8.4 mi / 13.4 km)
  • Triple Creek Winery (13.7 mi / 22.1 km)

Exploring the natural features in Trappe

Whether you're an outdoor enthusiast or just want to take in the scenery, Trappe is a great spot to appreciate mother nature. These are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city center:

  • Gerry Boyle Park at Great Marsh (5.3 mi / 8.5 km)
  • Long Wharf Park (5.8 mi / 9.3 km)
  • Blackwater National Wildlife Refuge (16.7 mi / 26.9 km)
  • Northern Chesapeake Bay (26.2 mi / 42.2 km)
  • Christ Rock Park (8.3 mi / 13.3 km)
  • Snows Turn Park (8.4 mi / 13.6 km)

How to get to and around Trappe

Fly into Easton, MD (ESN-Easton - Newnam), the closest airport, located 10.6 mi (17 km) from the city center. If you're unable to find a flight that fits your schedule, you can also fly into Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional), which is 36.5 mi (58.7 km) away.

Frequently asked questions

What are the best areas to stay in a vacation rental in Trappe?
Finding the right spot for your vacation in Trappe means considering the type of trip you have in mind. Vacation rentals in Trappe primarily consist of private homes, offering space and privacy for families and groups. These properties provide a comfortable base for exploring the local area, including natural attractions like Bill Burton Fishing Pier State Park, which is about 2 miles away, and cultural sites such as the Choptank River Lighthouse, approximately 3 miles from typical rental areas. For those interested in history, the Harriet Tubman Museum and Educational Center is about 3 miles away. The available vacation rentals in Trappe offer a relaxed setting, making them suitable for guests seeking a quiet retreat with convenient access to nearby points of interest.
What are the most popular vacation rentals in Trappe?
Vacation rentals in Trappe primarily feature houses, which are a popular choice for guests seeking ample space and privacy. These homes are well-suited for families and groups, providing comfortable living areas, multiple bedrooms, and often outdoor spaces for relaxation. Guests appreciate the ability to settle in and enjoy a home-away-from-home experience, whether for a short break or a longer stay.
What amenities do vacation rentals in Trappe usually offer?
Vacation rentals in Trappe come equipped with a variety of features designed for a comfortable stay. Guests can expect full kitchens, allowing for convenient meal preparation, along with free parking and high-speed internet access. Many properties also include air conditioning, ensuring comfort during warmer months, and offer outdoor areas such as balconies or patios for enjoying the fresh air. A selection of these vacation rentals also provides access to pools, adding an extra element of relaxation and fun to your trip.
Are there family-friendly vacation rentals in Trappe?
Families will find a selection of welcoming vacation rentals in Trappe, with several private homes designed to accommodate all ages. These properties often feature full kitchens for preparing family meals, along with outdoor play areas and games to keep children entertained. Many also include spacious dining areas, perfect for gathering together, and amenities like dishwashers to make cleanup easier after a day of exploring nearby parks or attractions.
Are there pet-friendly vacation rentals in Trappe?
For guests planning to bring their furry companions, one vacation rental in Trappe welcomes pets. This private home offers outdoor areas, providing space for pets to enjoy. It is a great option for those who want to include their pets in their travel plans and explore the natural surroundings of Trappe together.
What are the best areas for group vacation rentals in Trappe?
Groups planning a getaway to Trappe will find a few vacation rentals designed to accommodate larger gatherings, primarily consisting of private homes. These properties offer multiple bedrooms and bathrooms, ensuring comfort and convenience for everyone. Amenities often include spacious dining areas for shared meals, fully equipped kitchens for group cooking, and ample free parking. These features make it easy for groups to relax and enjoy their time together, whether for a family reunion or a friends' weekend.
What are the best luxury vacation rentals in Trappe?
For those seeking an elevated experience, Trappe offers a couple of upscale vacation rentals, primarily private homes. These properties often feature premium amenities such as private pools, providing an exclusive space for relaxation and enjoyment. Guests can also expect well-appointed outdoor areas, including balconies or patios, perfect for enjoying the serene surroundings. These luxury options are designed to offer enhanced comfort and privacy for a memorable stay.
Are there any budget-friendly vacation rentals in Trappe?
Guests looking for great value will find several budget-friendly vacation rentals in Trappe, mainly private homes. These properties offer essential amenities that help manage costs, such as full kitchens for preparing your own meals and laundry facilities for longer stays. Free parking and high-speed internet are also commonly available, adding to the overall value. Opting for a private home can be particularly cost-effective for groups or families, as the expense can be shared, providing more space for your budget.
Are there any vacation rentals in Trappe with a pool?
Yes, several vacation rentals in Trappe feature pools for guests to enjoy. These properties, predominantly private homes, offer refreshing outdoor pools, perfect for a swim on a warm day. A selection of these also includes private pools, providing an exclusive and secluded swimming experience. These amenities add a wonderful option for relaxation and fun during your stay in Trappe.
Are there any family-friendly vacation rentals in Trappe with a pool?
Families seeking vacation rentals with a pool in Trappe will find options that combine both comfort and fun. These family-friendly private homes often feature outdoor pools, providing a great way for everyone to cool off and play. Beyond the pool, these rentals typically include amenities like full kitchens for easy meal preparation, outdoor play areas, and games, ensuring a relaxing and entertaining stay for the whole family.
Are there any short-term vacation rentals in Trappe for a weekend getaway?
For a quick weekend getaway, vacation rentals in Trappe offer comfortable private homes that are ideal for short stays. These properties provide a convenient base to explore local attractions like Bill Burton Fishing Pier State Park, which is about 2 miles away, or the Choptank River Lighthouse, approximately 3 miles from typical rental areas. With amenities like full kitchens and comfortable living spaces, you can enjoy a relaxing and private retreat, making the most of your brief visit.
How early should I book a Trappe vacation rental?
Book your Trappe vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Trappe, Maryland, United States of America?
In Trappe, Maryland, visitors can enjoy a blend of natural beauty and local charm. The nearby Chesapeake Bay offers scenic waterfront views and opportunities for boating and fishing. The town's proximity to the picturesque Blackwater National Wildlife Refuge makes it an excellent spot for birdwatching and hiking, with trails that showcase the area's diverse wildlife and serene landscapes.For those interested in local history, the Trappe area features historic sites, such as the nearby town of Easton, known for its quaint shops and art galleries. The Talbot County Courthouse and the Academy Art Museum in Easton are top attractions that highlight the region's cultural heritage.
Can I change or cancel my Trappe home rental booking on Vrbo?
To find Trappe vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Trappe vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively. Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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