Trappe vacation rentals

We found 138 vacation rentals — enter your dates for availability

Discover a selection of vacation rentals in Trappe that are perfect for your trip. Whether you're staying in a vacation rental with your kids and pets or just with friends, you'll find the best amenities for hanging out with the people that matter most, which might include WiFi and a washer and dryer. You're sure to find a rental for everyone's needs, including places that are non-smoking or accessible.

Vacation rentals with weekly discounts - Trappe

Showing deals for:Jan 16 - Jan 23

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

Baja Deck with umbrella- sit in pool on plastic adirondack chairs and read!
10 out of 10, Exceptional, (137 reviews)
Exceptional
(137 reviews)

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

Easton, MD

9% off
Price is $1,057
$7,397 for 7 nights
All fees included
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks

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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.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your booking. Being the organizer has its perks. By enrolling in our travel rewards program, One Key, you can immediately access exclusive member discounts and earn OneKeyCash on eligible reservations. Sign up today and start enjoying your savings.

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:

  • Hog Neck Golf Course (11.5 mi / 18.5 km)
  • St. Michaels Winery (12.3 mi / 19.7 km)
  • Layton's Chance Vineyard and Winery (14.2 mi / 22.8 km)
  • Easton Cycle and Sport (8.2 mi / 13.2 km)
  • Triple Creek Winery (13.7 mi / 22.1 km)
  • Bay Country Shop (7 mi / 11.3 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)
  • Ragged Island (14.5 mi / 23.3 km)
  • Bruffs Island (15.4 mi / 24.8 km)
  • Christ Rock Park (8.3 mi / 13.3 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 is the best area to stay in Trappe when booking a vacation rental?
When planning a vacation rental in Trappe, Maryland, one of the best areas to consider is the charming neighborhood near the Choptank River. This picturesque location offers a serene atmosphere with beautiful waterfront views and easy access to outdoor activities. Staying here allows you to enjoy the tranquility of nature while still being close to town amenities.

A top attraction in this area is the historic town of Easton, just a short drive away. Easton is known for its vibrant arts scene, delightful shops, and excellent restaurants, making it an ideal spot for exploration and dining. Another point of interest is the nearby Oxford-Bellevue Ferry, which provides a scenic ride across the Tred Avon River and is a great outing for families or couples.

In terms of vacation rental options, this neighborhood typically offers a variety of properties, ranging from cozy cottages to spacious homes, accommodating different group sizes and preferences.
How much does it cost to rent a vacation home in Trappe?
Prices for vacation rentals in Trappe vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Trappe to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Trappe vacation house rentals?
You can find great discounts on house rentals in Trappe on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Trappe?
For renting a beach house in Trappe, Maryland, travelers should consider the nearby areas of Tilghman Island and Oxford, both of which offer charming waterfront properties with easy access to the Chesapeake Bay. On Tilghman Island, visitors can find cozy cottages and larger homes that often come with amenities such as private docks, outdoor decks, and expansive views of the water, ideal for fishing or kayaking enthusiasts. Many properties here also feature fully equipped kitchens and spacious living areas, great for family gatherings.

In Oxford, known for its historic charm, there are rentals that offer a blend of modern amenities and traditional coastal aesthetics. Travelers can expect properties with features like screened porches, private gardens, and direct access to small beaches along the Tred Avon River. This area is also home to local shops and eateries, providing a quaint atmosphere for leisurely strolls and dining.

Additionally, the nearby Blackwater National Wildlife Refuge offers opportunities for exploration and wildlife watching, enhancing the overall experience for those who enjoy nature. Rentals in this area often have outdoor spaces designed for relaxation, such as fire pits and picnic areas, making them suitable for enjoying the serene surroundings.
What is the most popular type of vacation rental accomodation in Trappe?
In Trappe, vacation houses and cottages are the most popular types of rental accommodations, with several available throughout the area. These properties are typically situated in serene settings, offering a peaceful retreat for travelers looking to explore the natural beauty of Maryland's Eastern Shore. Most vacation houses feature spacious living areas, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups. Cottages, on the other hand, often provide a cozy atmosphere with charming decor and outdoor spaces for relaxation.
Are there any family house rentals in Trappe?
In Trappe, Maryland, there are several family-friendly house rentals available, making it a lovely destination for groups looking to enjoy the area's charm. Many of these properties come equipped with spacious living areas, full kitchens for preparing meals, and comfortable bedrooms to accommodate families.

Visitors can also find outdoor spaces superb for relaxation and play, often featuring amenities like grills and fire pits for evening gatherings. The locale is close to the picturesque scenery of the Eastern Shore, where families can explore nearby parks and waterfront areas for activities such as hiking, fishing, or simply enjoying nature.
Can I rent a vacation home with a pool or hot tub in Trappe?
In Trappe, Maryland, there are several vacation homes available for rent that feature pools and hot tubs. This charming area offers a peaceful retreat with a mix of rural and waterfront properties, making it an ideal destination for relaxation. Travelers can expect various amenities in these rentals, including private pools for enjoying warm summer days, hot tubs for unwinding in the evenings, spacious outdoor areas, and fully equipped kitchens for preparing meals.
Can I find long-stay vacation rentals in Trappe?
A long-stay vacation rental in Trappe is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Trappe?
In Trappe, there are several pet-friendly house rentals available for travelers seeking a comfortable getaway. Many of these homes feature spacious layouts, fully equipped kitchens, and outdoor areas, making them ideal for families and groups who want to enjoy both relaxation and pet-friendly amenities. The rentals often include private yards, patios, and sometimes even access to nearby walking trails, superb for taking pets on leisurely strolls.

The surrounding area offers beautiful landscapes and outdoor activities, with easy access to local parks where pets can enjoy some fresh air and exercise.
Are there any remote work vacation rentals in Trappe?
In Trappe, Maryland, there are several remote work vacation rentals available that cater to the needs of professionals looking for a comfortable workspace. Many of these properties come equipped with essential amenities such as high-speed Wi-Fi, dedicated office spaces, ergonomic desk chairs, and desks that allow for a productive work environment.

The serene setting of Trappe provides a peaceful backdrop for remote work, with beautiful natural surroundings superb for taking breaks and enjoying the outdoors. Additionally, the area offers convenient access to nearby towns where you can find local dining options and shops. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Trappe vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Trappe with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Trappe?
In Trappe, popular vacation rental amenities include WiFi, kitchens, patios, coffee and tea makers, and decks or patios. Travelers can expect comfortable accommodations that allow them to prepare their own meals and enjoy the outdoors, whether it's sipping coffee on a private patio or enjoying a meal on the deck.
When is the best time to visit Trappe for a vacation rental?
The best time to visit Trappe for a vacation rental is during the peak summer months of June to August. This period attracts a lively crowd eager to enjoy the area's beautiful scenery and outdoor activities. With temperatures typically ranging from the low 70s to mid-80s Fahrenheit, visitors can relish the warm, inviting climate while exploring the picturesque landscapes of Maryland's Eastern Shore.

July, in particular, stands out as the most popular month. During this time, the charm of Trappe truly shines, offering an abundance of activities from kayaking on the Choptank River to wandering through local markets. The vibrant atmosphere makes it an ideal time for travelers, with plenty of opportunities for sightseeing and indulging in regional cuisine.

For those who prefer a more tranquil experience, consider visiting in December. This low season offers a unique charm, as you can enjoy the area's winter beauty and cozy accommodations at potentially lower rates. It's a great time for peaceful walks and enjoying the serene environment.

In summary, whether you choose the bustling summer months for fun and adventure or opt for the quiet beauty of winter, Trappe has something special to offer all year round.
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?
In Trappe, Maryland, visitors can enjoy a charming small-town atmosphere with several attractions nearby. The historic town is close to the picturesque Choptank River, where travelers can enjoy outdoor activities like fishing and kayaking. Just a short drive away, the town of Easton offers more cultural attractions, including art galleries, boutiques, and the Academy Art Museum. For those interested in nature, the Blackwater National Wildlife Refuge is within reach, providing opportunities for birdwatching and hiking in a diverse ecosystem.
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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
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.

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