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Middletown vacation rentals

We found 2,460 vacation rentals — enter your dates for availability

Discover a selection of 11 homes and other vacation rentals in Middletown that are perfect for your trip. Whether you're traveling with your kids or with friends, vacation homes have the amenities you need and want for your stay, which might include parking and a washer and dryer. No matter what you're looking for, you'll be sure to find a rental for everyone's needs, including a place that is accessible or non-smoking.

Vacation rentals with weekly discounts - Middletown

Showing deals for:Jul 3 - Jul 10

Image gallery for Waterfront property, perfect winter getaway, directly on the Willowemoc!

Front and yard
9.6 out of 10, Exceptional, (29 reviews)
Exceptional
(29 reviews)

Waterfront property, perfect winter getaway, directly on the Willowemoc!

Livingston Manor

13% off
Price is $222
$1,553 for 7 nights
All fees included
Waterfront property, perfect winter getaway, directly on the Willowemoc!

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Find out more about Middletown

Why visit Middletown

  • Family-friendly activities: Middletown offers a range of fun experiences suitable for all ages, making it an ideal vacation spot for families.
  • Outdoor adventures: Explore urban parks and nearby state parks, perfect for hiking, picnicking, and enjoying nature.
  • Bustling downtown: Discover the heart of Middletown in its vibrant downtown area, filled with local shops and friendly faces.
  • Diverse accommodations: Choose from budget-friendly options to luxury rentals, ensuring a comfortable stay for every traveler.
  • Local culture: Immerse yourself in the rich culture and community events that highlight the charm of Middletown.

Popular types of accommodation in Middletown

If you’re looking for the perfect getaway in Middletown, you’re in the right place. Our selection of vacation rentals includes houses, condos, and cozy cabins. Whether you’re interested in luxury homes with private pools or a charming retreat, we have an array of Middletown vacation rentals to suit your needs. Start your search for Middletown luxury rentals today and experience comfort and relaxation like never before.

  • Houses: The top choice among travelers, these spacious homes offer comfort and privacy, perfect for families or groups.
  • Condos: A popular selection, condos provide modern amenities and are often located near local attractions.
  • Cabins: Ideal for a rustic getaway, cabins immerse you in nature while offering a cozy retreat.
  • Cottages: These quaint accommodations are perfect for a charming and intimate experience.
  • Apartments: A convenient option, apartments offer flexibility and easy access to the city.**

Top attractions in and around Middletown

Middletown, New York, offers a delightful mix of family-friendly and entertainment-themed activities, perfect for any vacation. Visitors can explore urban parks and national state parks, while also enjoying the local culture. You'll find plenty of opportunities for outdoor adventures and family experiences, making it a great destination for all ages. Additionally, consider checking out rentals by neighborhoods to enhance your stay and discover the charm of this vibrant city.

  • Orange County Fairgrounds: Experience the lively atmosphere of this family-friendly venue, where you can enjoy various events, games, and delicious fair food, perfect for all ages.
  • Goshen Historic Track: Discover the excitement of horse racing at this historic track, offering thrilling races and a chance to immerse yourself in the sport in a vibrant atmosphere.
  • Orange County Arboretum: Stroll through beautifully landscaped gardens at this serene arboretum, ideal for families looking to connect with nature and enjoy outdoor activities.

Things to do recommended for couples

For a romantic getaway in Middletown, consider The Golf Club at Mansion Ridge, just 16 miles away. This luxurious country club offers a serene atmosphere perfect for couples looking to unwind and enjoy each other's company amidst beautiful landscapes.

Things to do recommended for families

Families visiting Middletown can explore the interactive exhibits at the Hudson Valley Science Center and enjoy outdoor fun at the local parks, such as Fancher-Davidge Park, which offers playgrounds and picnic areas perfect for a family day out.

Things to do recommended for groups

Groups visiting Middletown can enjoy a thrilling day at the nearby SplashDown Beach water park, explore the scenic trails at the nearby Wallkill River National Wildlife Refuge, or indulge in local flavors at the vibrant farmers market for a true taste of the region.

*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 Middletown

If you're traveling with a group, family, pets, or planning an extended stay, it's important to prioritize your preferences when filtering options. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to Middletown with a group: Think about how many bedrooms you require, along with amenities like a full kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for all these features and more on Vrbo.
  • Traveling to Middletown with young kids: Traveling with young children can be quite demanding. It's important to prioritize their comfort and safety, along with providing suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Middletown: For many families, a trip isn't truly enjoyable without their furry companions. If that resonates with you, consider exploring Vrbo properties that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Middletown: If you’re searching for vacation rentals that offer great deals for stays of a month or more, you’ve come to the right spot. By using the appropriate filters, 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 in and around Middletown

Explore the charming city of Middletown, New York, where family-friendly vibes meet vibrant entertainment. Discover the heart of Middletown in its bustling downtown area, filled with friendly people and diverse experiences. Nearby neighborhoods offer a mix of budget-friendly options and luxury accommodations, ensuring a delightful stay for every traveler. Whether you're looking for family activities or a taste of local culture, Middletown promises an unforgettable adventure.

  • Goshen: Located a mere 6 miles from Middletown, Goshen is a vibrant city that offers a delightful blend of family-friendly entertainment and urban charm. Visitors flock to Goshen for its popular shopping mall center, where a variety of retail options await. The city is also home to a renowned theme park, providing thrilling rides and attractions for all ages. Stroll through the picturesque tourist precinct and enjoy the lively atmosphere of the local square, making it an ideal destination for a fun-filled day out with family.
  • New Hampton: Just 3 miles away from Middletown, New Hampton is a charming city perfect for families seeking outdoor adventures. Known for its exciting water park and ski venues, this area offers a range of activities to keep everyone entertained. The nearby theme park is a hit with visitors of all ages, while the urban park provides a serene setting for leisurely walks and picnics. Whether you're looking to splash around or hit the slopes, New Hampton is a great spot for an action-packed getaway.
  • Washington Heights: Nestled within the Middletown area, Washington Heights is a quaint village that captures the essence of family and outdoor experiences. With its inviting shopping area and local theater, there's plenty to explore. Educational opportunities abound, making it not only entertaining but enriching as well. The village boasts a beautiful urban park, perfect for relaxation or a family outing, while the nearby tourist precinct and modern square offer additional attractions to enjoy. Washington Heights is a wonderful place to unwind and connect with the community.

Best time to go to Middletown

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

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January26.8°F (-2.9°C)Light RainMostly SunnySlightly LowAverage
February28.6°F (-1.9°C)Light RainMostly CloudyAverageSlightly Low
March36.1°F (2.3°C)Light RainMostly CloudyAverageSlightly Low
April47.5°F (8.6°C)Light RainMostly SunnySlightly HighSlightly Low
May58.5°F (14.7°C)Light RainMostly SunnyAverageAverage
June66.6°F (19.2°C)Light RainMostly SunnySlightly HighAverage
July72.7°F (22.6°C)Light RainMostly SunnySlightly HighSlightly High
August70.5°F (21.4°C)Light RainMostly SunnyAverageSlightly High
September63.7°F (17.6°C)Light RainMostly SunnyAverageAverage
October52.7°F (11.5°C)Light RainMostly SunnyAverageAverage
November40.6°F (4.8°C)Light RainMostly SunnySlightly LowAverage
December32.7°F (0.4°C)Light RainMostly CloudySlightly LowSlightly High

Booking with Vrbo is simple

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Also, extending your stay can lead to significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo's unique Trip Board offers you a convenient way to plan new trips, pick up right where you left off, and keep all your travel plans organized. You can easily access properties you've saved or booked under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Head to the friendly city of Middletown

Enjoy the area's churches, architecture and festivals and make a vacation rental your home during your stay in Middletown. This welcoming city allures visitors with its shopping and restaurants. Are you looking for specific amenities for your getaway? Many of our vacation rentals feature full kitchens and laundry facilities.

Activities and attractions in and around Middletown

Are you looking for attractions to see while you're in the area? Venture out of your vacation home and experience everything that makes Middletown a fun place to get away. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Goshen Historic Track (6.1 mi / 9.8 km)
  • LEGOLAND® New York (7.5 mi / 12 km)
  • Warwick Valley Winery and Distillery (10.7 mi / 17.2 km)
  • Brotherhood Winery (13.5 mi / 21.7 km)
  • Mount Peter Ski Area (15.3 mi / 24.6 km)
  • Holiday Mountain Ski and Fun Park (15.8 mi / 25.4 km)

Exploring the natural features in Middletown

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Middletown is a great place to get outside. Here are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city center:

  • Orange County Arboretum (8.1 mi / 13.1 km)
  • The Rock Sports Complex (10.3 mi / 16.5 km)
  • Masten Lake (12.6 mi / 20.3 km)
  • Neversink River (13.4 mi / 21.6 km)
  • Lake Louise Marie (14.2 mi / 22.9 km)
  • Sam's Point Preserve (15.7 mi / 25.3 km)

Traveling to and around Middletown

The nearest airport is in Stewart Intl. Airport (SWF), located 17.8 mi (28.7 km) from the city center.

Frequently asked questions

What is the best area to stay in Middletown, New York, United States of America when booking a vacation rental?
When looking for the best area to stay in Middletown, New York, consider the vibrant downtown neighborhood. This area is bustling with charm and offers a variety of vacation rental options, from cozy apartments to spacious homes. Staying downtown puts you within walking distance of several top attractions, such as the historic Paramount Theatre, which hosts a range of performances and events, and the local farmers' market, where you can enjoy fresh produce and artisanal goods.

Another great option is the surrounding residential areas, which provide a quieter atmosphere while still being close to the action. These neighborhoods typically offer a mix of single-family homes and multi-family units, giving visitors a chance to experience local life. Nearby, you can explore the scenic Wawayanda State Park, superb for hiking and enjoying nature, or visit the beautiful Wallkill River, which is ideal for leisurely walks and picnics.
How much does it cost to rent a vacation home in Middletown?
Prices for vacation rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Middletown 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 Middletown vacation house rentals?
You can find great discounts on house rentals in Middletown 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 Middletown ski resort rentals?
For ski resort rentals near Middletown, travelers should consider the nearby areas of the Catskills, particularly around towns like Monticello and Liberty, which are within a reasonable drive. These towns offer a selection of accommodations that cater to winter sports enthusiasts visiting the local ski resorts. Many properties feature cozy amenities such as fireplaces, ski storage, and fully equipped kitchens, making them superb for families or groups looking to enjoy a ski getaway.

In Monticello, visitors can find a range of vacation homes and lodges that provide easy access to the nearby resorts, with some properties offering scenic views of the surrounding mountains. Luxury options may include hot tubs, game rooms, and spacious living areas, ideal for unwinding after a day on the slopes.

Liberty, known for its quaint charm, also hosts several rental options including cabins and larger homes that often come with outdoor spaces for relaxing and enjoying the fresh mountain air. Being close to local dining and shopping options adds further convenience for guests.
What is the most popular type of vacation rental accomodation in Middletown?
In Middletown, a variety of vacation rental options are available, with vacation houses being particularly popular—several can be found throughout the area. These properties typically offer spacious layouts, multiple bedrooms, and fully equipped kitchens, making them ideal for families or larger groups. Many vacation houses also come with outdoor areas, such as patios or gardens, great for enjoying the fresh air.

Additionally, there are several cottages and cabins that provide a charming, rustic experience, often situated near nature trails and parks, allowing guests to immerse themselves in the beautiful surroundings. Campsites are also available for those looking to enjoy a more adventurous stay under the stars. For travelers preferring a more urban feel, several apartments can be found in Middletown, often featuring modern amenities and convenient access to local shops and restaurants.
Are there any family house rentals in Middletown?
In Middletown, New York, there are 14 family-friendly homes available, making it an excellent choice for those traveling with children. This charming town features properties that offer spacious living areas, full kitchens for preparing family meals, and often backyards or outdoor spaces for kids to enjoy. Many of these rentals come equipped with modern amenities such as Wi-Fi and air conditioning, ensuring a comfortable stay for everyone.

Visitors will find Middletown conveniently located near various attractions, including the scenic Hudson Valley and local parks, which provide opportunities for outdoor activities and family outings. The area is also home to shopping centers and dining options, allowing families to easily explore local cuisine and culture.
Can I rent a vacation home with a pool or hot tub in Middletown?
In Middletown, New York, there are several vacation homes available for rent that feature pools and hot tubs. This charming city in the Hudson Valley offers a variety of accommodations suitable for travelers looking to relax and enjoy some leisure time. Many of these properties come equipped with private swimming pools, hot tubs, and spacious outdoor areas great for gatherings or family fun. Inside, you can expect amenities like fully equipped kitchens, comfortable living spaces, and modern conveniences to make your stay enjoyable. Find your rental in Middletown with a pool or a hot tub.
Can I find long-stay vacation rentals in Middletown?
A long-stay vacation rental in Middletown 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 Middletown?
In Middletown, there are several pet-friendly house rentals available, making it a great destination for travelers looking to enjoy a stay with their furry companions. Many of these vacation homes offer amenities such as spacious backyards, fully equipped kitchens, and cozy living areas, ensuring comfort for both humans and pets.

The area is also close to various parks and outdoor spaces, providing ample opportunities for walks and playtime with pets. Nearby, the scenic Wawayanda State Park features hiking trails and open areas that are superb for exploring with your dog, allowing for an enjoyable outdoor experience.
Are there any remote work vacation rentals in Middletown?
In Middletown, New York, there are several remote work-friendly vacation rentals available, totaling around 15 options. These accommodations are well-suited for travelers looking to combine work and leisure. Properties typically offer amenities such as free Wi-Fi, dedicated office spaces, and comfortable work areas, ensuring that guests can stay productive during their stay. Many rentals include additional conveniences like fully equipped kitchens, allowing for easy meal preparation, and living spaces designed for relaxation after a day of work.

Middletown itself boasts a variety of attractions, including nearby parks for outdoor activities and local dining options that showcase the regional cuisine. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Middletown vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Middletown 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 Middletown?
In Middletown, popular rental amenities include kitchens, which allow travelers to prepare their meals, and decks or patios that provide outdoor space for relaxation and enjoying the fresh air. Many rentals are pet-friendly, permitting guests to bring their furry companions along for the stay. Additionally, service animals are welcomed, ensuring that those with specific needs are accommodated. Onsite parking is also a common feature, making it convenient for guests with vehicles.
When is the best time to visit Middletown for a vacation rental?
The peak season for visiting Middletown is during the summer months, from June to August. This vibrant period attracts travelers eager to enjoy outdoor adventures, local festivals, and the warm, inviting atmosphere that Middletown is known for. July is particularly popular, with an array of activities and events that create a lively environment for visitors.

During these months, you can expect pleasant temperatures ranging from the mid-70s to low 80s Fahrenheit, making it ideal for exploring the charming downtown area or taking part in outdoor activities like hiking in the nearby Hudson Valley. The summer also offers opportunities to visit local farmers' markets, where you can sample fresh produce and artisanal goods, enhancing your experience in the area.

For those looking for a more budget-friendly option, consider visiting in December. While this month is part of the low season, it allows you to experience a quieter side of Middletown, complete with festive holiday decorations and a cozy atmosphere. You'll find great deals on vacation rentals and a chance to enjoy seasonal events and local traditions without the hustle and bustle of peak tourist traffic.

Ultimately, the best time to visit Middletown for a vacation rental depends on your preferences for activity and atmosphere.
How early should I book a Middletown vacation rental?
Book your Middletown 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 Middletown, New York, United States of America?
In Middletown, New York, visitors can enjoy a variety of attractions that showcase the area's charm. The downtown area features a historic Main Street with local shops, cafes, and restaurants, great for a leisurely stroll. Nearby, the Paramount Theatre offers a mix of live performances and film screenings, making it a cultural hub for entertainment.

For nature enthusiasts, the scenic Wawayanda State Park is just a short drive away, providing hiking trails, picnic areas, and opportunities for fishing or boating on the lake. The nearby Wallkill River National Wildlife Refuge is another great spot for outdoor activities, offering trails for walking and wildlife observation.

Families can also visit the Orange County Fairgrounds, which hosts events throughout the year, including the popular Orange County Fair in the summer. The area's rich history can be explored at the Middletown Thrall Library, which often features local exhibits and programs.
Can I change or cancel my Middletown home rental booking on Vrbo?
To find Middletown 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 Middletown 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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