With great scenery and majestic nature surrounding it, Middletown in Orange County, New York, is a sight to behold. You will never be bored in this idyllic and charming town, as it is filled to the brim with great locations with flora and fauna. There are fantastic things to do and place to see here. Yearly events such as the Orange County Fair and the Orange County Fair Speedway also happen here. It is a great place to stay as you get to explore and visit many of the various communities surrounding Middletown such as Crystal Run, Fair Oaks, Pilgrim Corners, Town of Wallkill, Washington Heights, and many more. Check out theatres, art galleries, bowling alleys, and much more. Middletown is also the home to many dairy farms, therefore you can always be sure of great views when you visit. Just sit back and scroll down for the top Airbnb vacation rentals in Middletown, New York.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on February 06, 2024.
1. Large abode featuring a Chinese-style garden (from USD 161)
Welcome to this adorable house, a unique and charming haven idyllic for families. Its authentic Chinese-style backyard garden enclosed by a full fence sets the mood for hosting small gatherings or simply basking in the sun’s embrace. In the living room, you can curl up with a good read as the wood-burning fireplace fills the space with cozy warmth. The interior also boasts a spacious dining room and a large kitchen with a center island, which both come in handy for bonding over great food.
Surrendering to a snooze in the private bedrooms with plush beds and picturesque outdoor views feels extra rewarding. With free parking available for at least three cars in the driveway, convenience is at your fingertips if your group is arriving in batches.
Top guest reviews
Amenities & Room:
nice kitchen area and a big table that was perfect to spread out and be productiveCleanliness:
the house was very cleansuper accommodating and house was very cleana clean and inviting space in a charming town in the catskill mountains just outside nycRead more reviewsHost:
the hosts were super responsive easy to communicate and very laid back
2. Hudson Lodge - Port Jervis (from USD 113)
This pet-friendly Airbnb in Middletown named Hudson Lodge - Port Jervis boasts modern and convenient furnishing that caters to both short and long getaways. With two queen-size beds, it provides comfortable accommodations for small families or groups. Each bedroom features its own smart TV, ensuring uninterrupted streaming in private. But if the whole crew is up for a movie night together, the living room with a 65-inch smart TV is just the perfect spot.
The kitchen of this two-bedroom apartment in Middletown is stocked with essential appliances and cookware to facilitate all your home-style meal requirements. Outdoors, you’ll spot a deck complete with a propane grill as well as a fire pit accompanied by a fire starter kit and an ample supply of wood for delightful evenings under the stars.
Top guest reviews
Amenities & Room:
beds were super comfyliving room was a good size and the couch was incredibly comfortablevery comfortable living space thoughthe bed was perfect and we both got great night’s sleepbeautiful cozy stay perfect size for a small family or romantic getaway will definitely be backCleanliness:
house was clean plenty of towels and toiletriesbeds and bedding was super clean and comfygood communication place was very clean would stay again for sureclean fully stocked very nice place to staynice clean and quiet place to stay with my familyHost:
the host was very friendly and communicativeRead more reviewsLocation:
this middletown ny location was wonderfulgreat location easy check in with key padthis location in a quiet neighborhood is perfect for a small familygreat location to meet up with friends and explore downtown middletownthis place has a great location not far from the city but it still allows for a good getaway
3. Comfy unit ideal for backpackers (from USD 72)
Are you a solo traveler looking for a spacious and clean place to stay? Here’s your answer. With a single bed, this place is very comfy, modern, and airy. There are Wi-Fi services, dryer, heating, air conditioning, washing machine, free parking, well-equipped kitchen, and more. For those on business travel, there is also a workspace for you to use. It is also close to a medical facility.
Top guest reviews
Amenities & Room:
the lights and ac were remote controlled and there is a desk and wifi perfect to work atCleanliness:
room was clean and comfya clean accommodation and pleasant greeterthe accommodations are clean and simplepretty nice area very quiet and cleanclean room quiet area polite hostsHost:
the host was nice and understandingboyang and his wife are extremely sweet hosts with a lovely home in a great locationvery kind hosts and a very comfortable roomgreat host who has interesting stories about falungthis place was a great value hosts were friendly and checkin was super easy would stay againRead more reviewsLocation:
nice warm place around 2 miles away from the medical schoolgreat place for a low price in middletown
4. Great stay for a small family (from USD 132)
Traveling with your family of four? Then look no further than this house. Offering a gorgeous view of the New York skyline, this house boasts an indoor fireplace, cable TV services, Wi-Fi services, heating, air conditioning, and many more. It is also child-friendly, with kids’ books and toys, children’s tableware, as well as babysitter recommendations. The kitchen is fully equipped with refrigerator, microwave, stove, and more. Plus, you will also have your own entrance to the premises.
Top guest reviews
Amenities & Room:
the room was a good size and the bed very comfortableCleanliness:
the room is very clean with all essentialsthe bathroom was clean and well equipped toovery nice communicative and super cleanthe house and the room we stayed in was clean warm and comfortableplace was cozy and cleanHost:
kimberly is so kind and welcoming and her home was lovelykimberly and her husband are kind and wonderful peoplekimberly and family are super warm and amazing hostskimberly was very welcoming and kind to uskimberly was great at communicating and friendlyRead more reviewsLocation:
the neighborhood was so nice and in a great locationkimberly's place is a great place to stay if you're in the middletown areanice area for a walkthe neighborhood is wonderful and i found it to be quite quietnice place in à nice quiet safe neighborhood which was just what i wanted
5. Stylish and classy house (from USD 119)
This retreat can fit up to six and is a modern and spacious abode. There is a dryer and a washer as well as a kitchen for your convenience during your stay. Apart from that, the house is only a short drive away from many places including the towns of Middletown, Wallkill, Patterson, and Warwick. Wi-Fi, cable TV services, and free parking spots are also made available at this house for rent in Middletown.
Top guest reviews
Amenities & Room:
a beautiful house with lots of room and comfortable sleeping arrangementshuge added bonus is the large washer and dryer in the bathroomthe beds were extremely comfortablealso the beds were very comfortableCleanliness:
wonderfully clean and cozyvery clean and well maintained houseclean and up to dateclean and easy to useit was clean stylish and comfortableHost:
the host is very responsivegreat host quick responses highly recommendshe was so helpful and nice thank youRead more reviewsLocation:
beautiful area centrally located to places we wanted to visitwe really enjoyed our stay at skye’s placewe also loved the calm and peaceful locationbeds are comfortable and close to things we were interested in seeingthis please was a great location to come back to especially after being in the big city
6. Room in a strategically located house
This unit, fit for one, is located in a house in the middle of a large green yard. Its secluded location makes it a favorite among visitors to Middletown since it is away from all the traffic and noise but is still close enough to all the happenings in the town. You get a fully equipped kitchen, a flat-screen TV, Wi-Fi services, a gas grill, as well as a private 10-acre (4 hectares) forested landscape around the house. Many attractions like hot air balloon rides in the Lower Hudson Valley, Castle Fun Centre, and many more are a short distance away.
Middletown, New York, United States
4.03 km (2.6 mi) from Soons OrchardsAccommodates: 1
Top guest reviews
Amenities & Room:
when you stay at ramon's not only will you get a great room for an incredible priceCleanliness:
the entire place is really clean and homely feeling also it smells greatvery clean and fantastic value for the price ramon is very hospitable and friendlyhis dogs are quiet and well-behaved and the room is cleanRead more reviewsHost:
super friendly host very accommodatingi loved staying here ramon was a great host and has a lovely homeramon is by far the most thoughtful and caring host i have ever methe’s got three dogs all friendly and niceas a bonus it is pet friendly and ramon himself has great dogs
7. Comfortable basement studio nearby the town
This one-bedroom basement studio can house one person and is designed in a very spacious and comfy way. The unit has a private entrance, as well as a private bathroom, microwave, fridge, Wi-Fi, and cable TV services. You will only be three minutes away from the Middletown downtown, where great restaurants, pubs, cafés, entertainment centers, and many more can be found. You also get one freeload in the laundry room. The house also has a big yard in case you feel like spending time out in the sun.
Middletown, New York, United States
3.54 km (2.2 mi) from Soons OrchardsSuperhostAccommodates: 1
Top guest reviews
Read more reviewsAmenities & Room:
it’s a simple space that’s cozy and comfortable
8. Abode with a majestic mountain view
Housing up to six people at one time, this house boasts remarkable views for guests. It gives majestic vistas of the mountain and the woods surrounding it right from your doorstep. It has three rooms, two bathrooms, and a well-equipped spacious kitchen. The house also has a pool and a patio for a great day out in the sun and it is also very accessible to various attractions in the town. Moreover, guests can also enjoy Wi-Fi access during your stay here.
11.23 km (7.0 mi) from Soons OrchardsAccommodates: 6
Top guest reviews
Amenities & Room:
the view is beautiful and the patio with the pool was just amazinggreat place lots of space & views from pool are amazingthe wifi wasn't strong but it was a nice break from technologythe kitchen space was great house is clean and the mattresses were very comfortable including the air mattressthe house is really nice with a huge kitchen and living roomCleanliness:
space was clean and tidyit was really clean and quietvery nice and clean househubert’s place is clean and spaciousthe place was clean and niceHost:
hubert was a great host overallhubert was a great hosthighly recommend this house and this hosthubert is a wonderful hosthubert was very responsive with any questions i hadRead more reviewsLocation:
good location if you’re staying in the middletown areagreat location spacious living room and beautiful kitchenit is an ideal place to retirethe auto outside light comes on once close to the house after the first time it's easierthe location was beautiful - just like the pictures posted and very quiet area
9. Accommodation for every type of tourist
This stay is guaranteed to satisfy almost all types of travelers. If you love nature, this house is very close to some great places. If you love shopping, many shopping areas are just a drive away. Cleanliness of the house, excellent amenities, as well as the friendly host are some things you can look forward to here. Housing up to four comfortably, this house has Wi-Fi services, cable TV services, as well as free parking on the premises.
4.87 km (3.1 mi) from Soons OrchardsAccommodates: 4
Top guest reviews
Cleanliness:
very clean spacebathroom was clean plenty of towels providedthe bed was very comfortable and bathroom was clean with fresh towels and washclothsvery clean and the house is in a new subdivisiongreat condo clean and spacious barbara was super nice and totally coolHost:
barbara is a wonderful friendly host loves to chat and welcomed me to her lovely homebarbara is a gracious and lively host with a colorful historyresident doggie super nice friendly and cuddlybarbara has a great personality and was very helpfulterrific host and the puppy(cush) is so cute friendly and sweet tooRead more reviewsLocation:
so thankful to be able to find this place at the last minute on a holiday weekend
10. Chic and elegant unit for three
This trendy abode is suitable for three and has its own entrance. It is perfect for those visiting Middletown for an outdoor adventure vacation, as it is very adjacent to many hiking trails and places to explore. Apart from that, you can also visit wineries and the countryside to have a more relaxing day out. It comes with Wi-Fi, TV, heating, free parking, kitchen appliances, and more. The Middletown city center, where all the action happens, is just 10 minutes away.
Middletown, New York, United States
13.01 km (8.1 mi) from Soons OrchardsTop guest reviews
Read more reviews
Book a stay in Middletown
With so many accommodation options available, from guesthouses to cheap condo rentals, Middletown is a place where finding the perfect stay wouldn’t be much of a chore. So don’t wait anymore, all you’ve got to do is pick a place from the list and go on a memorable vacation now!
If you think your trip to Middletown will be awkwardly short, why not extend the escapade to a nearby village, in a similarly comfortable and convenient retreat? There are Airbnb vacation rentals in Montecillo that are great gateways to excellent Big Apple thrills. And if you’re traveling with kids, you can include Legoland New York Resort in your itinerary and stay awhile in an Airbnb vacation rental in Goshen.
Frequently asked questions about the Airbnb vacation rentals in Middletown, New York
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