List your Property
Middletown, New York, United States of America

Middletown holiday rentals

We found 924 holiday rentals — enter your dates for availability

Discover a selection of 1,000 holiday home rentals in Middletown, NY, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Stayz holiday homes have the best amenities for hanging out with the people that matter most, including pool and private pool. Prices start at AU$ 402 per night, and holiday houses and cabins are popular options for a stay in Middletown. Either way, you'll find holiday accommodation for everyone's needs.
DynamicDestinationRefinements
AsyncDestinationUrgency
Find spaces that suit your style

Houses

View 695 Houses

Cabins

View 136 Cabins

Bungalows

View 113 Bungalows

Cottages

View 113 Cottages

Condos/Apartments

View 95 Condos/Apartments

Farmhouses

View 18 Farmhouses

Chalets

View 23 Chalets

Studios

View 32 Studios
Top rated rentals — Middletown
Stayed Apr 2021

Amazing Stay

My family and I absolutely enjoyed our visit. The view was amazing and the reality of the place matched exactly with the pictures. We have 4 small children under the age of ten years old, and they enjoyed putting their feet in the lake and collecting...

Raggia S.
Raggia S.
Stayed Mar 2021

Cute, Cozy, Comfortable cabin

We really enjoyed our stay here. The cabin had everything we needed. Enioyed hiking at Stokes and High Point and coming back to a cozy fire and playing games. The decor was perfect for the place. Loved all the little details. Such a charming place. W...

Kristen H.
Kristen H.
Stayed Mar 2021

Idyllic riverside retreat with superb hosts

You see a common thread about Chris and David being superb hosts, and it's 100% true. Chris made sure we knew all the ins and outs of the apartment when we checked in. David gave me fishing tips and even gifted me a fishing lure - and I managed to ca...

Lei Z.
Lei Z.

New York City, USA

Stayed Mar 2021

Celebration weekend

Our group had a wonderful time during out stay. We had an outdoor birthday brunch, including pickeball on the very well maintained tennis court and an easter egg hunt in the front yard. The kitchen was well equipped with serving platters and the thre...

Lily P.
Lily P.
Stayed Mar 2021

Midweek getaway

We had a short stay with Joseph as a mini-vacay to break the monotony of covid life. The house is way off the beaten path but the amenities are top notch. Spotlessly clean and truly a breath of fresh air. If you cook, the kitchen has EVERYTHING! The ...

Fab G.
Fab G.
Stayed Mar 2021

Perfect peaceful getaway

My friend and I stayed here to be close to hiking at Minnewaska State Park. What a lovely place to land after an 8 hour hike! The sunset over the lake was beautiful, the house had everything we needed. We spent a day enjoying the lake, grilling and r...

Kira K.
Kira K.
Stayed Feb 2021

Great Girls Weekend!

We stayed here for a long weekend to celebrate our friends birthday and it was such a great weekend!! The owner met us at the house to check us in and was very helpful on giving us information on things we might want to do during our stay. The house ...

Christine P.
Christine P.
Stayed Feb 2021

Exactly as pictured

My 3 friends and I enjoyed our stay. It was a long weekend low-key getaway from the city and the home and area provided the things that we needed. The house was exactly as pictured and the four of us were comfortable in the space. Jack was very respo...

Angie S.
Angie S.

New York, NY

AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy
Destination guide

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. Whether you're planning a family holiday, a trip with friends or a romantic retreat, Stayz has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities

Activities and attractions in Middletown

Are you looking for top things to see and do while you're in the area? Venture out of your cosy holiday rental and experience everything that Middletown has to offer. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Orange County Fairgrounds (1.5 mi / 2.4 km)
  • Soons Orchards (3.1 mi / 4.9 km)
  • Goshen Historic Track (5.9 mi / 9.5 km)
  • Castle Fun Center (9.1 mi / 14.6 km)
  • Warwick Valley Winery and Distillery (10.7 mi / 17.2 km)
  • Scenic Farms Golf Course (11 mi / 17.8 km)
Natural highlights

Exploring the natural landscape of Middletown

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

  • Thomas Bull Memorial Park (8 mi / 12.9 km)
  • The Rock Sports Complex (10.1 mi / 16.3 km)
  • Pine Island Town Park (10.6 mi / 17.1 km)
  • Frederick Franck's Pacem in Terris (14.1 mi / 22.7 km)
  • Arrow Park Lake and Lodge (16.7 mi / 26.9 km)
  • Mary H Harriman Memorial Park (17.1 mi / 27.6 km)
How to get there

Transport options to and around Middletown

Fly into Newburgh, NY (SWF-Stewart Intl.), the closest airport, located 17.7 mi (28.5 km) from the city centre.

How many holiday accommodation are available around Middletown?

Our 2021 accommodation listings offer a large selection of 924 holiday rentals around Middletown. From 695 holiday houses to 136 cabins, find unique holiday homes for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay around Middletown is on Stayz.

Can I rent Houses in Middletown?

Yes, of course. Stayz offers 695 Houses in Middletown. Our other popular types of Middletown holiday rentals include:

  • Cabins: 136 holiday houses
  • Bungalows: 113 holiday houses
  • Cottages: 113 holiday houses

But you can also enjoy a great stay in one of our other holiday rentals including Condos/Apartments and more.

Can I find a holiday accommodation with pool in Middletown?

Yes, you can select your preferred holiday accommodation with pool among our 278 holiday homes with pool available in Middletown. Please use our search bar to access the selection of holiday rentals available.