Middletown holiday lettings

We found 2,432 holiday rentals — enter your dates for availability

Discover a selection of 13 homes and other holiday rentals in Middletown that are perfect for your trip. Whether you're going on holiday with family or friends, holiday homes have the best amenities for hanging out with the people that matter most, which might include a garden and pool. Whatever you're looking for, you'll be sure to find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - Middletown

Showing deals for:13 Mar - 20 Mar

Image gallery for complete privacy vacation home [private pool]

Pool
10 out of 10, Exceptional, (11 reviews)
Exceptional
(11 reviews)

complete privacy vacation home [private pool]

Newburgh, NY

11% off
Price is £5,115
for 7 nights, 1 home
£731 per night
includes taxes & fees
complete privacy vacation home [private pool]

Find spaces that suit your style

Head to the friendly city of Middletown

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

Activities and attractions in and around Middletown

Are you searching for attractions to see during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that Middletown has to offer. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • 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)
  • City Winery Hudson Valley (11.7 mi / 18.9 km)
  • Brotherhood Winery (13.5 mi / 21.7 km)
  • Mount Peter Ski Area (15.3 mi / 24.6 km)

Exploring the natural features in Middletown

Whether you're an adventurous traveller or just want to appreciate the scenery, Middletown is a great place to get out in nature. These are some of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • The Rock Sports Complex (10.3 mi / 16.5 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)
  • Arrow Park Lake and Lodge (16.9 mi / 27.2 km)
  • Greenwood Lake (18.7 mi / 30.1 km)

Travelling to and around Middletown

The nearest airport is in Newburgh, NY (SWF-Stewart Intl.), located 17.8 mi (28.7 km) from the city centre.

Frequently asked questions

What is the best area to stay in Middletown when booking a holiday rental?
When considering a holiday rental in Middletown, New York, a popular area to stay is the downtown neighbourhood. This vibrant area offers a charming mix of local shops, cafes, and restaurants, making it a delightful place to explore on foot. Staying here provides convenient access to top attractions such as the historic Paramount Theatre, which frequently hosts live performances and events, as well as the scenic Wallkill River, great for those who enjoy outdoor activities like walking or cycling.
How much does it cost to rent a holiday home in Middletown?
Prices for holiday 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 holiday 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 those seeking ski resort rentals near Middletown, New York, the nearest ski area is the Mountain Creek Resort, located approximately 30 minutes away in Vernon, New Jersey. In this vicinity, travellers can find a variety of accommodation options, including cozy lodges and chalets that cater to winter sports enthusiasts. Many of these properties offer amenities like ski storage, fireplaces, and hot tubs, providing a comfortable retreat after a day on the slopes.

In addition to Mountain Creek, the nearby town of Greenwood Lake offers charming cabins and holiday homes, often featuring scenic lake views and easy access to hiking trails. These rentals typically come equipped with modern conveniences such as full kitchens, outdoor spaces, and sometimes even fireplaces for a warm and inclusive setting.
What is the most popular type of holiday rental accomodation in Middletown?
In Middletown, holiday houses are the most popular type of accommodation, with around 11 available throughout the area. These holiday houses typically feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or groups seeking a comfortable stay. Many of these properties also include outdoor spaces for relaxation, such as gardens or patios. Additionally, there are several campsites, cottages, and cabins, each offering a great experience for travellers looking to connect with nature or enjoy a rustic retreat. Apartments are also available, providing a more compact option for those wanting to explore the local attractions.
Are there any family house rentals in Middletown?
In Middletown, New York, there are some family-friendly house rentals available, with around 14 options to choose from. This charming town offers a variety of accommodations that cater well to families. Many properties feature spacious living areas, fully equipped kitchens for preparing meals together, and outdoor spaces where children can play safely.
Can I rent a holiday home with a pool or hot tub in Middletown?
In Middletown, New York, there are several holiday homes available for rent that feature pools and hot tubs, making it an appealing destination for travellers seeking relaxation and leisure. This charming town, located in the scenic Hudson Valley region, offers a variety of properties, including spacious family homes and cosy retreats.
Can I find long-stay holiday rentals in Middletown?
A long-stay holiday rental 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Middletown?
In Middletown, New York, there are several pet-friendly house rentals available, with a total of eleven options for travellers. Many of these properties offer amenities that cater to both comfort and convenience, featuring spacious living areas, fully equipped kitchens, and outdoor spaces where pets can roam freely.
Are there any remote work holiday rentals in Middletown?
In Middletown, New York, there are ample options for remote work holiday rentals, with around 17 available throughout the area. These properties typically come equipped with amenities tailored for productivity, including high-speed Wi-Fi, dedicated desks, office chairs, and safe spaces conducive to working from home. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Middletown holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals 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 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 typically include features such as kitchens equipped with microwaves and dishwashers, allowing guests to prepare meals during their stay. Many rentals also offer comfortable living areas, which provide a welcoming space for relaxation after exploring the local attractions.
When is the best time to visit Middletown for a holiday rental?
The best time to visit Middletown for a holiday rental is during the summer months, specifically from June to August. This peak season attracts travellers, drawn by the warm weather and a variety of outdoor activities. With temperatures typically hovering in the mid to high 20s Celsius, it's ideal for exploring local parks, hiking trails, and enjoying the vibrant community events that pop up throughout the summer.

July is particularly popular, as the town buzzes with energy and offers a lot of activities, from local festivals to outdoor concerts. This lively atmosphere is superb for those looking to connect with other travellers while indulging in the seasonal delights of Middletown.

If you're considering a budget-friendly option, visiting in December can be a wonderful choice. Although this month falls outside the high tourist season, it presents a charming holiday ambiance with festive decorations and local events that capture the spirit of the season. The crisp winter air can be invigorating, providing a different but equally enchanting experience of the town.
How early should I book a Middletown holiday rental?
Book your Middletown 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.
Can I change or cancel my Middletown home rental booking on Vrbo?
To find Middletown 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 Middletown 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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