Trappe holiday lettings

We found 137 holiday rentals — enter your dates for availability

Discover a selection of holiday rentals in Trappe that are perfect for your trip. Whether you're staying in a holiday rental with family, friends or just your furry companion, you'll find the amenities that you need and want, which might include parking and a garden. You're sure to find a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

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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 holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Trappe

Are you looking for things to do while you're in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Trappe a one-of-a-kind holiday spot. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • 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)
  • Talbot Massage (8.4 mi / 13.4 km)
  • Hog Neck Golf Course (11.5 mi / 18.5 km)
  • Phillips Wharf Environmental Center (15.2 mi / 24.5 km)

Exploring the natural features in Trappe

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your holiday in Trappe. These are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • 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)
  • 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 centre. 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 holiday rental?
When considering a holiday rental in Trappe, Maryland, the area around Easton is an excellent choice. Easton, located just a short drive away, offers a charming blend of history and modern amenities. You will find a variety of holiday rental properties suiting different preferences, from quaint cottages to more spacious homes.

One of the top attractions in Easton is the Academy Art Museum, which showcases a diverse collection of artworks and hosts engaging exhibitions throughout the year. Additionally, the picturesque waterfront area along the Tred Avon River provides lovely walking paths and dining options, making it a delightful spot to relax and enjoy the scenery.

Staying in this area gives you easy access to not only Trappe but also the surrounding Talbot County, where you can explore beautiful landscapes and enjoy outdoor activities.
How much does it cost to rent a holiday home in Trappe?
Prices for holiday 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 holiday 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, consider the nearby areas along the picturesque shores of the Chesapeake Bay. The towns of Easton and Oxford, both just a short drive away, offer charming waterfront properties with stunning views of the bay. Many of these homes come equipped with amenities such as private docks, outdoor seating areas, and expansive decks great for enjoying the sunset over the water.

In Easton, visitors can find a selection of spacious houses ideal for families, featuring modern kitchens, multiple bedrooms, and access to local beaches. Additionally, properties in Oxford often provide a quaint, village atmosphere, with some rentals offering kayaks or paddleboards for exploring the calm waters.

Travellers can also enjoy the nearby public beaches and parks, such as the Oxford Beach, which features picnic areas and a sandy shoreline for relaxing days by the water. For those looking to immerse themselves in local culture, downtown Easton boasts delightful shops, galleries, and restaurants, providing a great blend of leisure and exploration during a beach getaway.
What is the most popular type of holiday rental accomodation in Trappe?
In Trappe, holiday houses and cottages are the most popular types of holiday rentals, with several options available in this charming area. These properties are typically situated in serene surroundings, superb for those looking to escape the hustle and bustle. Most holiday houses feature spacious layouts, multiple bedrooms, and fully equipped kitchens, allowing guests to enjoy a comfortable and home-like experience. Cottages, on the other hand, provide a cozier atmosphere, often with rustic decor and intimate 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 suitable destination for those travelling with children. Many of these homes are located in picturesque neighbourhoods close to the scenic Eastern Shore, offering easy access to local attractions. Visitors can expect spacious living areas, fully equipped kitchens for family meals, and outdoor spaces where children can play and explore.

The nearby areas, such as Easton and St. Michaels, provide additional points of interest, including charming shops, waterfront parks, and historical sites. Properties often include amenities such as Wi-Fi, air conditioning, and sometimes even outdoor patios or gardens for relaxation.
Can I rent a holiday home with a pool or hot tub in Trappe?
In Trappe, Maryland, there are several holiday homes available for rent that feature pools or hot tubs. This charming area is known for its picturesque surroundings and offers a tranquil escape for travellers. Many of the properties come equipped with amenities that enhance the experience, such as private pools, spacious outdoor areas for relaxation, and hot tubs great for unwinding after a day of exploration. Additionally, these homes often include fully equipped kitchens, allowing guests to prepare meals during their stay.
Can I find long-stay holiday rentals in Trappe?
A long-stay holiday rental in Trappe is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there any remote work holiday rentals in Trappe?
In Trappe, Maryland, there are several remote work holiday rentals available, making it a great choice for those looking to balance work and leisure. Many of these properties come equipped with essential amenities for remote work, including Wi-Fi, dedicated desk spaces, and even office facilities that can be booked for meetings or focused work sessions.

The area is picturesque, offering a serene environment that can help enhance productivity. Travellers can also enjoy local attractions, including beautiful waterfront views and nearby parks, which provide opportunities for relaxation during breaks. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Trappe holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Trappe with parking available—perfect for families or travellers 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 holiday rentals typically feature several desirable amenities that enhance the comfort of guests. Most properties come equipped with a kitchen, allowing travellers to prepare their own meals and enjoy home-cooked dining. Many rentals also offer outdoor spaces such as patios or decks, ideal for relaxing in the fresh air. A fireplace is a common feature, providing a cosy atmosphere during cooler evenings. Additionally, onsite parking is available, making it convenient for those travelling by car.
When is the best time to visit Trappe for a holiday rental?
The best time to visit Trappe for a holiday rental is during the peak season from June to August. This vibrant period attracts visitors keen to enjoy the warm summer weather and partake in various outdoor activities, such as kayaking on the Choptank River or exploring the beautiful landscapes of the Eastern Shore.

July stands out as the most popular month, with plenty of sunshine and temperatures typically ranging from the mid-teens to low 30s Celsius. It's an excellent time for families and friends to gather, as the community comes alive with events and festivities that highlight the charm of this quaint Maryland town.

For those seeking more economical options, consider planning your visit in December. While this month falls outside the bustling summer season, it offers a unique opportunity to enjoy a quieter atmosphere, with fewer crowds and the chance to experience Trappe's charming holiday decorations and local festivities.
How early should I book a Trappe holiday rental?
Book your Trappe holiday 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 holiday 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 mix of natural beauty and historic charm. One of the top attractions is the nearby Blackwater National Wildlife Refuge, which offers exceptional opportunities for birdwatching and exploring scenic trails. This area is great for nature enthusiasts and provides a tranquil escape into the outdoors.

The town itself has a quaint atmosphere, with local shops and eateries that reflect its small-town character. Nearby, the historic town of Easton features charming architecture and a vibrant arts scene, including galleries and theatres that often host performances and exhibitions.

Additionally, the Chesapeake Bay is just a short drive away, offering stunning waterfront views and opportunities for boating, fishing, and enjoying fresh seafood at local restaurants.
Can I change or cancel my Trappe home rental booking on Vrbo?
To find Trappe holiday 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 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 travellers 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 cosy cabin or a beach house, 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 holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, 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 organising 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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