Top 10 Airbnb Vacation Rentals In Middletown, New York - Updated 2024

Durgahyeni
Durgahyeni 
Updated
| 4 min read

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.

Stayed at this property?
Middletown, New York, United States
5.72 km (3.6 mi) from Soons Orchards
49 reviews   Wifi Available
ENTIRE HOME 3 Beds 5 Guests 3 Bedrooms 1 Bathrooms

Accommodates: 5

Top guest reviews
Amenities & Room:
nice kitchen area and a big table that was perfect to spread out and be productive
Cleanliness:
the house was very clean
super accommodating and house was very clean
a clean and inviting space in a charming town in the catskill mountains just outside nyc
Host:
the hosts were super responsive easy to communicate and very laid back
Read more reviews

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.

Stayed at this property?
Middletown, New York, United States
4.87 km (3.1 mi) from Soons Orchards
104 reviews   Superhost Wifi Available
ENTIRE HOME 2 Beds 4 Guests 2 Bedrooms 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
beds were super comfy
living room was a good size and the couch was incredibly comfortable
very comfortable living space though
the bed was perfect and we both got great night’s sleep
beautiful cozy stay perfect size for a small family or romantic getaway will definitely be back
Cleanliness:
house was clean plenty of towels and toiletries
beds and bedding was super clean and comfy
good communication place was very clean would stay again for sure
clean fully stocked very nice place to stay
nice clean and quiet place to stay with my family
Host:
the host was very friendly and communicative
Location:
this middletown ny location was wonderful
great location easy check in with key pad
this location in a quiet neighborhood is perfect for a small family
great location to meet up with friends and explore downtown middletown
this place has a great location not far from the city but it still allows for a good getaway
Read more reviews

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.

Stayed at this property?
Middletown, New York, United States
6.59 km (4.1 mi) from Soons Orchards
55 reviews   Wifi Available
PRIVATE ROOM IN HOME 1 Bed 1 Guest 1 Bedroom 1 Bathrooms

Accommodates: 1

Top guest reviews
Amenities & Room:
the lights and ac were remote controlled and there is a desk and wifi perfect to work at
Cleanliness:
room was clean and comfy
a clean accommodation and pleasant greeter
the accommodations are clean and simple
pretty nice area very quiet and clean
clean room quiet area polite hosts
Host:
the host was nice and understanding
boyang and his wife are extremely sweet hosts with a lovely home in a great location
very kind hosts and a very comfortable room
great host who has interesting stories about falung
this place was a great value hosts were friendly and checkin was super easy would stay again
Location:
nice warm place around 2 miles away from the medical school
great place for a low price in middletown
Read more reviews

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.

Stayed at this property?
Middletown, New York, United States
6.73 km (4.2 mi) from Soons Orchards
25 reviews   Wifi Available
PRIVATE ROOM IN HOME 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
the room was a good size and the bed very comfortable
Cleanliness:
the room is very clean with all essentials
the bathroom was clean and well equipped too
very nice communicative and super clean
the house and the room we stayed in was clean warm and comfortable
place was cozy and clean
Host:
kimberly is so kind and welcoming and her home was lovely
kimberly and her husband are kind and wonderful people
kimberly and family are super warm and amazing hosts
kimberly was very welcoming and kind to us
kimberly was great at communicating and friendly
Location:
the neighborhood was so nice and in a great location
kimberly's place is a great place to stay if you're in the middletown area
nice area for a walk
the neighborhood is wonderful and i found it to be quite quiet
nice place in à nice quiet safe neighborhood which was just what i wanted
Read more reviews

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.

Stayed at this property?
Middletown, New York, United States
13.13 km (8.2 mi) from Soons Orchards
127 reviews   Wifi Available
ENTIRE RENTAL UNIT 3 Beds 6 Guests 1 Bedroom 1 Bathroom

Accommodates: 6

Top guest reviews
Amenities & Room:
a beautiful house with lots of room and comfortable sleeping arrangements
huge added bonus is the large washer and dryer in the bathroom
the beds were extremely comfortable
also the beds were very comfortable
Cleanliness:
wonderfully clean and cozy
very clean and well maintained house
clean and up to date
clean and easy to use
it was clean stylish and comfortable
Host:
the host is very responsive
great host quick responses highly recommend
she was so helpful and nice thank you
Location:
beautiful area centrally located to places we wanted to visit
we really enjoyed our stay at skye’s place
we also loved the calm and peaceful location
beds are comfortable and close to things we were interested in seeing
this please was a great location to come back to especially after being in the big city
Read more reviews

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.

Stayed at this property?
Middletown, New York, United States
4.03 km (2.6 mi) from Soons Orchards
12 reviews   Wifi Available
PRIVATE ROOM IN HOME 1 Bed 1 Guest 1 Bedroom 1 Bathroom

Accommodates: 1

Top guest reviews
Amenities & Room:
when you stay at ramon's not only will you get a great room for an incredible price
Cleanliness:
the entire place is really clean and homely feeling also it smells great
very clean and fantastic value for the price ramon is very hospitable and friendly
his dogs are quiet and well-behaved and the room is clean
Host:
super friendly host very accommodating
i loved staying here ramon was a great host and has a lovely home
ramon is by far the most thoughtful and caring host i have ever met
he’s got three dogs all friendly and nice
as a bonus it is pet friendly and ramon himself has great dogs
Read more reviews

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.

Stayed at this property?
Middletown, New York, United States
3.54 km (2.2 mi) from Soons Orchards
11 reviews   Superhost Wifi Available
Entire townhouse 1 Bed 1 Guest 1 Bedroom 1 Bathroom

Accommodates: 1

Top guest reviews
Amenities & Room:
it’s a simple space that’s cozy and comfortable
Read more reviews

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.

Stayed at this property?

11.23 km (7.0 mi) from Soons Orchards
137 reviews   Wifi Available
ENTIRE HOME 3 Beds 6 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 6

Top guest reviews
Amenities & Room:
the view is beautiful and the patio with the pool was just amazing
great place lots of space & views from pool are amazing
the wifi wasn't strong but it was a nice break from technology
the kitchen space was great house is clean and the mattresses were very comfortable including the air mattress
the house is really nice with a huge kitchen and living room
Cleanliness:
space was clean and tidy
it was really clean and quiet
very nice and clean house
hubert’s place is clean and spacious
the place was clean and nice
Host:
hubert was a great host overall
hubert was a great host
highly recommend this house and this host
hubert is a wonderful host
hubert was very responsive with any questions i had
Location:
good location if you’re staying in the middletown area
great location spacious living room and beautiful kitchen
it is an ideal place to retire
the auto outside light comes on once close to the house after the first time it's easier
the location was beautiful - just like the pictures posted and very quiet area
Read more reviews

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.

Stayed at this property?

4.87 km (3.1 mi) from Soons Orchards
9 reviews   Wifi Available
PRIVATE ROOM IN HOME 2 Beds 4 Guests 1 Bedroom 1 Bathrooms

Accommodates: 4

Top guest reviews
Cleanliness:
very clean space
bathroom was clean plenty of towels provided
the bed was very comfortable and bathroom was clean with fresh towels and washcloths
very clean and the house is in a new subdivision
great condo clean and spacious barbara was super nice and totally cool
Host:
barbara is a wonderful friendly host loves to chat and welcomed me to her lovely home
barbara is a gracious and lively host with a colorful history
resident doggie super nice friendly and cuddly
barbara has a great personality and was very helpful
terrific host and the puppy(cush) is so cute friendly and sweet too
Location:
so thankful to be able to find this place at the last minute on a holiday weekend
Read more reviews

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.

Stayed at this property?
Middletown, New York, United States
13.01 km (8.1 mi) from Soons Orchards
5 reviews  
Entire guest suite 1 Bed 1 Bedroom 1 Bathroom
Top guest reviews
Cleanliness:
very nice and clean place
very clean and respectful host
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.

Stayed at this property?

Frequently asked questions about the Airbnb vacation rentals in Middletown, New York

1. Which Airbnb vacation rentals in Middletown are suitable for families?

For a comfortable stay with the whole family in Middletown, you can consider properties such as these: i) large abode featuring a Chinese-style garden, ii) Hudson Lodge - Port Jervis, and iii) stylish and classy house.

2. Which Airbnb vacation rentals in Middletown have parking?

To help you get easily settled upon arrival, you can check out some of these properties with car parking facilities: i) stylish and classy house, ii) large abode featuring a Chinese-style garden, iii) Hudson Lodge - Port Jervis, or iv) comfy unit ideal for backpackers.

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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A simple writer, a wanderlust addict. I am Durga, a writer by profession and an addict of wanderlust by nature. I love world culture, urban spaces, wildlife, architectural ruins and every part...Read more

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