Middletown holiday rentals

We found 133 holiday rentals — enter your dates for availability
Discover a selection of 7 homes and other holiday rentals in Middletown that are perfect for your trip. Whether you're travelling with family, friends or just your furry companion, holiday rentals have the best amenities for hanging out with the people that matter most, such as parking and air conditioning. What you'll find is a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

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Take in the riverfront beauty of Middletown

Enjoy the entertainment and other features of Middletown. Well known for its golfing, fishing and basketball games, this walkable city won't disappoint. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in Middletown

Do you want to find top things to see and do while you're in the area? Venture out of your cosy holiday rental and check out everything that makes Middletown a one-of-a-kind holiday spot. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Big Cork Vineyards (6.4 mi / 10.2 km)
  • Catoctin Wildlife Preserve and Zoo (11.8 mi / 19.1 km)
  • Worthington Manor Golf Club (12 mi / 19.4 km)
  • Whiskey Creek Golf Club (14.2 mi / 22.8 km)
  • Tarara Winery (14.8 mi / 23.8 km)
  • Adventure Park USA (14.9 mi / 24 km)

Exploring the natural landscape of Middletown

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

  • Baker Park (7.1 mi / 11.4 km)
  • Greenbrier State Park (7.7 mi / 12.3 km)
  • Carroll Creek Linear Park (8 mi / 12.9 km)
  • Crystal Grottoes Caverns (8 mi / 12.9 km)
  • Sugarloaf Mountain Park (15.6 mi / 25 km)
  • Buckeystown Community Park (10.6 mi / 17 km)

How to get to and around Middletown

Fly into Hagerstown, MD (HGR-Hagerstown Regional), the closest airport, located 20.6 mi (33.2 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could also fly into Martinsburg, WV (MRB-Eastern West Virginia Regional), which is 24 mi (38.6 km) away.

Frequently asked questions

What is the best area to stay in Middletown when booking a holiday rental?
When considering a holiday rental in Middletown, Maryland, the charming historic district is a popular area to stay. This picturesque neighbourhood is known for its quaint streets lined with well-preserved 19th-century buildings, providing a delightful backdrop for your visit. You'll find a variety of holiday rentals here, ranging from cosy cottages to spacious homes, making it an appealing choice for families or couples alike.One of the highlights of staying in this area is the proximity to the Civil War-era landmarks, which offer fascinating insights into the region's rich history. Additionally, the nearby Washington Monument State Park provides stunning views and excellent hiking opportunities, great for outdoor enthusiasts. The local dining scene is also worth exploring, with several charming cafes and restaurants that showcase the area's culinary delights.
What is the most popular type of holiday rental accomodation in Middletown?
In Middletown, holiday houses are the most popular type of holiday rental, with about 15 available throughout the area. These rentals typically offer spacious living areas, multiple bedrooms, and fully equipped kitchens, ideal for families or groups seeking comfort and convenience. Additionally, there are several cabins and cottages that provide a more rustic experience, often situated in scenic locations, great for enjoying nature. Apartments are also available, offering a more compact and modern stay.
Are there any family house rentals in Middletown?
In Middletown, Maryland, there are several family-friendly house rentals available, making it an appealing choice for those travelling with children. The area is known for its picturesque landscapes and proximity to outdoor activities. Many of these homes feature spacious living rooms, full kitchens to prepare family meals, and outdoor areas superb for kids to play in.Visitors can explore local parks, such as the nearby Middletown Park, which offers playgrounds and walking trails. Additionally, the charming town centre boasts quaint shops and restaurants, providing a taste of local culture and cuisine.
Can I rent a holiday home with a pool or hot tub in Middletown?
In Middletown, Maryland, there are several holiday homes available for rent that come with pools or hot tubs, making it an appealing choice for travellers seeking relaxation and comfort. This charming town, located in the scenic Appalachian Mountains, offers a selection of properties that provide both indoor and outdoor amenities. Many rentals feature private pools, hot tubs, spacious patios, and well-equipped kitchens, ideal for unwinding after a day of exploring the local area.The surrounding landscape also enhances the experience, as Middletown is known for its beautiful parks and access to outdoor activities, including hiking and biking trails.
Are there pet-friendly house rentals in Middletown?
In Middletown, Maryland, there are several pet-friendly house rentals available, making it a great choice for travellers looking to bring their furry companions along. Many of these holiday homes offer amenities such as spacious backyards, allowing pets to roam freely, and comfortable living spaces designed for relaxation.The area itself is picturesque, surrounded by scenic landscapes, and offers easy access to nearby parks where you can enjoy outdoor activities with your pets. One such location is the Middletown Park, which features walking trails and green spaces great for leisurely strolls. Additionally, the charming downtown area of Middletown has various pet-friendly cafes and shops, ideal for both you and your pet.
Are there any remote work holiday rentals in Middletown?
In Middletown, Maryland, there are numerous holiday rentals suitable for remote work, with around 30 options available. This quaint town offers a peaceful environment, ideal for those looking to blend work and leisure. Many properties come equipped with high-speed internet and Wi-Fi, ensuring a reliable connection for remote tasks.Travellers can expect amenities such as comfortable workspaces, dedicated offices, and well-furnished living areas. Some rentals even feature outdoor spaces where you can enjoy fresh air during breaks.Middletown's charming historic district is nearby, providing convenient access to local shops and cafes for a change of scenery during the workday. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Middletown?
In Middletown, popular rental amenities include fireplaces, which create a warm and inviting atmosphere. Many properties come equipped with full kitchens, allowing guests to prepare their own meals during their stay. Pet-friendly options are also available, making it convenient for travellers who wish to bring their furry companions. Onsite parking is a common feature, providing ease of access for guests with vehicles. Additionally, air conditioning is often included, ensuring comfort during the warmer months.
When is the best time to visit Middletown for a holiday rental?
April marks the beginning of the peak season in Middletown, where visitors can bask in the beauty of spring while enjoying a range of outdoor activities. From April to June, this charming town attracts those eager to explore its scenic landscapes and vibrant local culture. The mild temperatures during this time, typically ranging from 10 to 20 degrees Celsius, create a comfortable environment superb for hiking, cycling, and leisurely strolls through the picturesque streets.April is particularly popular due to the delightful bloom of flowers and the vibrant greenery that transforms the area. Visitors can take advantage of local events, such as farmers' markets and spring festivals, which showcase the best of Middletown's community spirit and local produce. The inviting atmosphere is ideal for families and couples looking to immerse themselves in nature and enjoy quality time together.If you are seeking a more budget-friendly option, March offers a quieter experience with fewer crowds, making it a great time to explore the historical sites and enjoy the early signs of spring without the hustle and bustle of peak tourist activity. This month provides a unique opportunity to appreciate the charm of Middletown at a more relaxed pace.Ultimately, the best time to visit Middletown depends on whether you prefer the vibrant energy of peak season filled with activities and events or the tranquil beauty of early spring for a more laid-back getaway.
What are the top attractions in Middletown?
In Middletown, Maryland, visitors can discover a range of attractions that highlight the area's historical charm and natural beauty. The historic Main Street is lined with quaint shops and eateries, offering a glimpse into the town's rich past. Nearby, the Middletown Valley is a picturesque setting for outdoor enthusiasts, featuring scenic hiking trails and beautiful landscapes, particularly in the South Mountain State Park, which is a short drive away and provides ample opportunities for hiking and wildlife viewing.The area is also known for its proximity to the National Historic District of Boonsboro, where visitors can explore sites related to the Civil War and enjoy local arts and crafts. Additionally, the annual Middletown Heritage Festival is a highlight, celebrating the community's culture with live music, food vendors, and local artisans.
Are all fees included in the Middletown holiday homes prices shown on Stayz?
Stayz 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.
Are there any Middletown holiday homes with parking?
Stayz offers a wide selection of holiday homes in Middletown 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 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.
Are there any discounts for Middletown holiday homes?
You can find great discounts on holiday homes in Middletown on Stayz, 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.
Can I change or cancel my Middletown holiday home booking on Stayz?
To find Middletown holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Middletown?
A long-stay holiday home in Middletown 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Middletown holiday home?
Book your Middletown holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Middletown?
Prices for holiday homes in Middletown 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Middletown to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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