Search Apartments in Middletown

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Middletown apartments

TV

Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
10.0 out of 10, Exceptional, (1 review)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is HK$729
HK$1,487 total
includes taxes & fees
2 Feb - 3 Feb
Cozy 1-bedroom retreat minutes from West Point!
Fridge, oven, stovetop, coffee/tea maker

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.8 out of 10, Exceptional, (15 reviews)
"Great Unit."
United States
Rudy R.
The price is HK$585
HK$2,011 total
includes taxes & fees
19 Jan - 20 Jan
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
1 bedroom

Natural Getaway at Orchard Farm Lakeside Retreat

Natural Getaway at Orchard Farm Lakeside Retreat
2.0 star property
Monroe
The price is HK$757
HK$1,852 total
includes taxes & fees
19 Jan - 20 Jan
Natural Getaway at Orchard Farm Lakeside Retreat
3 bedrooms, desk, iron/ironing board, travel cot

Local Artist Inspired | Walk to WestPoint + King Bed

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
9.2 out of 10, Wonderful, (10 reviews)
"Great place to stay if you have a West Point student - super close to all West Point related activities. The place itself needs some work but it’s functional."
United States
Jesse C.
The price is HK$608
HK$2,787 total
includes taxes & fees
20 Jan - 21 Jan
Local Artist Inspired | Walk to WestPoint + King Bed
Dining

Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
Beacon
10.0 out of 10, Exceptional, (32 reviews)
"Great time and great place to stay "
United States
S S.
The price is HK$873
HK$1,858 total
includes taxes & fees
19 Jan - 20 Jan
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
Interior

Dream getaway apartment in the foot of Gunks Ridge

Dream getaway apartment in the foot of Gunks Ridge
Wallkill
9.6 out of 10, Exceptional, (24 reviews)
"Over all the property was clean and staff was very cooperative. Only problems were the beds were very hard which made it hard for us to get a good nights sleep. The larger room had bugs but the owner took care of it right away. We enjoyed our stay."
United States
Harriet
The price is HK$453
HK$1,291 total
includes taxes & fees
20 Jan - 21 Jan
Dream getaway apartment in the foot of Gunks Ridge
Exterior detail

Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen

Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
Beacon
9.8 out of 10, Exceptional, (42 reviews)
"Adorable place to stay in an adorable town! "
United States
Mary L.
The price is HK$858
HK$1,822 total
includes taxes & fees
20 Jan - 21 Jan
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
Interior

Lux APT Your home away from home.

Lux APT Your home away from home.
Beacon
10.0 out of 10, Exceptional, (2 reviews)
"Very clean and great place to stay. "
United States
Charlene D.
The price is HK$1,107
HK$2,126 total
includes taxes & fees
1 Feb - 2 Feb
Lux APT Your home away from home.
Exterior detail

Cozy Studio with WiFi and AC in enjoyable Glen Spey

Cozy Studio with WiFi and AC in enjoyable Glen Spey
Glen Spey
The price is HK$842
HK$1,693 total
includes taxes & fees
19 Jan - 20 Jan
Cozy Studio with WiFi and AC in enjoyable Glen Spey
1 bedroom, free WiFi, bed sheets, wheelchair access

Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen

Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
Warwick
10.0 out of 10, Exceptional, (34 reviews)
"Great location within walking distance of boutiques and restaurants. Enjoyed our stay. "
United States
Cynthia W.
The price is HK$936
HK$2,029 total
includes taxes & fees
20 Jan - 21 Jan
Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
Desk, WiFi, bed sheets

Studio Retreat | Near Woodbury Commons & Legoland

Studio Retreat | Near Woodbury Commons & Legoland
2.0 star property
Monroe
The price is HK$616
HK$1,565 total
includes taxes & fees
19 Jan - 20 Jan
Studio Retreat | Near Woodbury Commons & Legoland
Terrace/patio

Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley

Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley
Highland
10.0 out of 10, Exceptional, (1 review)
"Everyone was just right! The home is perfect for a photo shoot. We weren't there for that, but we thought the setting was unique and beautiful! Everything we needed!!"
United States
Rebecca D.
The price is HK$1,287
HK$2,961 total
includes taxes & fees
16 Jan - 17 Jan
Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley
1 bedroom

Bright Studio Retreat w Deck Nature Views

Bright Studio Retreat w Deck Nature Views
2.0 star property
Monroe
The price is HK$1,150
HK$2,558 total
includes taxes & fees
19 Jan - 20 Jan
Bright Studio Retreat w Deck Nature Views
Fridge, microwave, oven, stovetop

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Highland Falls
10.0 out of 10, Exceptional, (5 reviews)
"Very nice property. We have a son at West Point and approximately an hour from New York City. Host was quick to respond to questions and provided excellent information. We will stay here again. "
United States
Mark V.
The price is HK$1,318
HK$2,349 total
includes taxes & fees
9 Feb - 10 Feb
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Exterior detail

Treeview - Cozy 2 BR Apartment - Fast WiFi ~ 1 hr from NYC - 5 mins to downtown

Treeview - Cozy 2 BR Apartment - Fast WiFi ~ 1 hr from NYC - 5 mins to downtown
Port Jervis
10.0 out of 10, Exceptional, (6 reviews)
"House was clean and parking was easy! Close to downtown Port Jervis, with some great restaurants. The owners were so kind, and were so helpful!"
United States
Jen C.
The price is HK$775
HK$2,407 total
includes taxes & fees
22 Jan - 23 Jan
Treeview - Cozy 2 BR Apartment - Fast WiFi ~ 1 hr from NYC - 5 mins to downtown
1 bedroom, desk, iron/ironing board, free WiFi

Charming 1-bedroom apartment. Pet-friendly. Hiking & Skiing 10 min way.

Charming 1-bedroom apartment. Pet-friendly. Hiking & Skiing 10 min way.
Wurtsboro
9.0 out of 10, Wonderful, (2 reviews)
"The host was very welcoming and very responsive. The apartment was very cute and super clean. I came up for a Halloween event put on by a friend the location was very convenient in the downtown area and I could walk to most of the places I needed to get to I very much enjoyed my stay here and would stay again if I’m in the area. "
United States
Sheena C.
The price is HK$1,014
HK$2,130 total
includes taxes & fees
21 Jan - 22 Jan
Charming 1-bedroom apartment. Pet-friendly. Hiking & Skiing 10 min way.
Microwave, oven, stovetop, dishwasher

Modern Hudson Valley Apt 202 - King/Queen/Twin

Modern Hudson Valley Apt 202 - King/Queen/Twin
Montgomery
9.8 out of 10, Exceptional, (16 reviews)
"We had a great stay!! I booked for a “get ready” spot for my wedding and it was everything I could have dreamed of. Everything was perfect and very clean! Can’t wait to book again Very centrally located near some amazing small boutiques, a couple restaurants. The town seemed like a popular spot on the weekend! "
United States
Tiffani H.
The price is HK$1,175
HK$2,106 total
includes taxes & fees
19 Jan - 20 Jan
Modern Hudson Valley Apt 202 - King/Queen/Twin
TV

Walk to WP Gate + Free Parking!

Walk to WP Gate + Free Parking!
Highland Falls
9.8 out of 10, Exceptional, (21 reviews)
"This place was awesome for the location to Thayer gate, close to restaurants, and a parking spot next to the building. We will return to this place!"
United States
Pamela
The price is HK$1,114
HK$2,070 total
includes taxes & fees
18 Jan - 19 Jan
Walk to WP Gate + Free Parking!
Property grounds

Villa Verde B&B, Greenwood Lake NY, 1

Villa Verde B&B, Greenwood Lake NY, 1
Monroe
10.0 out of 10, Exceptional, (31 reviews)
"Great host. Home is very clean and well appointed. Would definitely stay here again."
United States
Thomas
The price is HK$1,224
HK$2,082 total
includes taxes & fees
16 Jan - 17 Jan
Villa Verde B&B, Greenwood Lake NY, 1
Outdoor dining

Cozy 1-bedroom apartment with AC, WiFi in charming Port Jervis

Cozy 1-bedroom apartment with AC, WiFi in charming Port Jervis
Port Jervis
10.0 out of 10, Exceptional, (1 review)
"Great communication, easy check in, great location, what more could you ask for?"
United States
Joseph F.
The price is HK$1,326
HK$2,011 total
includes taxes & fees
16 Jan - 17 Jan
Cozy 1-bedroom apartment with AC, WiFi in charming Port Jervis
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middletown Hotel Reviews

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury

10/10 Excellent
"Clean and the staff are very nice "
Jeanette 1-night trip
Posted 2 days ago
Hampton Inn Harriman Woodbury

Find out more about Middletown

Middletown Apartments information

Number of reviews
235
Accommodation
147 Apartments
Lowest Price
HK$1,291
Highest Price
HK$2,961

Frequently asked questions

What's it like to stay at an apartment in Middletown?
You'll find a lot of options for your stay in Middletown with 44 accommodation options. Though there aren't many apartments, we can help you locate accommodation that is similar. When you search on Expedia, you can use the filters to search for a kitchen— one of the conveniences often found in an apartment. You can also search for similar property types like holiday homes, condos or cabins. You might want to visit the area's shops and enjoy its restaurants.
Why would you choose an apartment over a traditional hotel room?
An apartment features a kitchen for convenient meals, and often has more space than a traditional hotel room. Apartments are a good option for solo travellers who want to stay in at night and plan out their next day, and also for families wanting the conveniences of home.
What's a favourite apartment for my stay in Middletown?
Below is a popular apartment to consider: Cottage Suites: Includes free WiFi . Free parking and on-site laundry facilities are on site .
What can I expect from the weather in Middletown?
Weather is only one factor, but it can really affect your travel plans, especially if you're planning an extended stay in Middletown. The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Middletown are January, February, March and April, with each month seeing an average of 16 cm of snowfall.
What should I see in Middletown?
Middletown is known for its restaurants and shops. Highland Lake and Thomas Bull Memorial Park are a couple of scenic spots to enjoy the outdoors, whereas Paramount Theatre is one of the cultural attractions. Other places in town to visit include Orange County Fair Speedway and Orange County Fairgrounds.
What's the best way to get to and around Middletown?
Knowing a bit about the transportation options can you save you a headache when you get to your destination. Fly into Newburgh, NY (SWF-Stewart Intl.), which is located 17.8 mi (28.7 km) away from the city centre. If you'd like to venture out around the area, you may want a rental car for your journey.

Explore a world of travel with Expedia