Top 8 Airbnb Vacation Rentals In Middletown, New York - Updated 2022

airbnb middletown ny

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. 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.

1. Stylish and classy house (from USD 139)

This house 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 is also available, as are cable TV services and free parking spots.

Just Around The Corner
Middletown, New York, United States
107 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
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
the host is very responsive
great host quick responses highly recommend
she was so helpful and nice thank you
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

2. Accommodation for every type of tourist (from USD 150)

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.

9 reviews  Wifi Available
Private room in home 2 Beds 4 Guests 1 Bedroom 1 Bathrooms

Accommodates: 4

Top guest reviews
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
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
so thankful to be able to find this place at the last minute on a holiday weekend
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3. Comfy unit for one guest (from USD 68)

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.

亦樂朋來 A The ancient legend civilization
Middletown, New York, United States
45 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
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
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
nice warm place around 2 miles away from the medical school
great place for a low price in middletown
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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.

New York Skyline - Private - near Downtown- Touro
Middletown, New York, United States
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
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
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
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
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5. 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.

Cozy & central apartment: come, be refreshed
Middletown, New York, United States
5 reviews
Entire guest suite 1 Bed 1 Bedroom 1 Bathroom
Top guest reviews
very nice and clean place
very clean and respectful host
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.

Spacious Single Bedroom in Middletown, NY (Room 2)
Middletown, New York, United States
12 reviews
Private room in house 1 Bed 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
when you stay at ramon's not only will you get a great room for an incredible price
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
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.

Dee and Dane’s Cozy Basement
Middletown, New York, United States
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
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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.

Mountain View House
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
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
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
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

Book a stay in Middletown

With so many great places to see, witness, and explore in this truly charming town, Middletown is a place that you would want to add to your travel list. 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!

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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