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Check prices for these dates

In two weeks
6 Feb - 8 Feb
In two months
20 Mar - 22 Mar
In three months
17 Apr - 19 Apr
In four months
15 May - 17 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 AED 343
AED 701 total
includes taxes & fees
4 Feb - 5 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, (16 reviews)
"Great Unit."
United States
Rudy R.
The price is AED 275
AED 947 total
includes taxes & fees
25 Jan - 26 Jan
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Apartment | 1 bedroom

Studio Lakeside Retreat Fast Wifi Great WFH

Studio Lakeside Retreat Fast Wifi Great WFH
2.0 star property
Monroe
The price is AED 339
AED 852 total
includes taxes & fees
25 Jan - 26 Jan
Studio Lakeside Retreat Fast Wifi Great WFH
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 AED 404
AED 884 total
includes taxes & fees
25 Jan - 26 Jan
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
3 bedrooms, desk, iron/ironing board, travel crib

Local Artist Inspired | Walk to WestPoint + King Bed

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
9.4 out of 10, Exceptional, (11 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 AED 320
AED 1,350 total
includes taxes & fees
27 Jan - 28 Jan
Local Artist Inspired | Walk to WestPoint + King Bed
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)
"Serg’s place was comfortable and clean! It was a perfect location for me and my friends to stay while rock climbing in the Gunks. We did not feel cramped or unsafe and the complementary tea was a hit! One thing to note is that both of the beds were low to the ground (below knee level) so if someone has knee or back problems, it might be difficult to stand up out of bed. "
United States
Mary S.
The price is AED 200
AED 594 total
includes taxes & fees
25 Jan - 26 Jan
Dream getaway apartment in the foot of Gunks Ridge
Interior

Luxe Loft on Main St.ZeroG King Bed, Designer Kitchen, Elevator!

Luxe Loft on Main St.ZeroG King Bed, Designer Kitchen, Elevator!
Warwick
10.0 out of 10, Exceptional, (42 reviews)
"This loft is great! Well appointed with everything you need. "
United States
Jean L.
The price is AED 400
AED 918 total
includes taxes & fees
2 Feb - 3 Feb
Luxe Loft on Main St.ZeroG King Bed, Designer Kitchen, Elevator!
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, (43 reviews)
"Adorable place to stay in an adorable town! "
United States
Mary L.
The price is AED 404
AED 858 total
includes taxes & fees
25 Jan - 26 Jan
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
Exterior

Studio Retreat | Near Woodbury Commons & Legoland

Studio Retreat | Near Woodbury Commons & Legoland
Monroe
The price is AED 275
AED 722 total
includes taxes & fees
25 Jan - 26 Jan
Studio Retreat | Near Woodbury Commons & Legoland
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 AED 357
AED 1,155 total
includes taxes & fees
26 Jan - 27 Jan
Treeview - Cozy 2 BR Apartment - Fast WiFi ~ 1 hr from NYC - 5 mins to downtown
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 AED 606
AED 1,395 total
includes taxes & fees
25 Jan - 26 Jan
Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley
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 AED 477
AED 999 total
includes taxes & fees
25 Jan - 26 Jan
Charming 1-bedroom apartment. Pet-friendly. Hiking & Skiing 10 min way.
Apartment | 1 bedroom

Bright Studio Retreat w Deck Nature Views

Bright Studio Retreat w Deck Nature Views
2.0 star property
Monroe
The price is AED 474
AED 1,128 total
includes taxes & fees
26 Jan - 27 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 AED 575
AED 1,037 total
includes taxes & fees
4 Feb - 5 Feb
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
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 AED 496
AED 964 total
includes taxes & fees
10 Feb - 11 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 AED 397
AED 813 total
includes taxes & fees
2 Feb - 3 Feb
Cozy Studio with WiFi and AC in enjoyable Glen Spey
1 bedroom, desk, iron/ironing board, free WiFi

Luxury New 1BR 950 sq ft apartment. Sleeps 4. Stocked Kitchen, 2 Tvs, Parking.

Luxury New 1BR 950 sq ft apartment. Sleeps 4. Stocked Kitchen, 2 Tvs, Parking.
Montgomery
10.0 out of 10, Exceptional, (3 reviews)
"Wonderful stay. Responded quickly to any issues even if it was a tiny one. Would absolutely stay here again. "
United States
Richard D.
The price is AED 545
AED 983 total
includes taxes & fees
9 Feb - 10 Feb
Luxury New 1BR 950 sq ft apartment. Sleeps 4. Stocked Kitchen, 2 Tvs, Parking.
Outdoor dining

The Appalachian at Mountain Creek

The Appalachian at Mountain Creek
Vernon Township
The price is AED 430
AED 886 total
includes taxes & fees
28 Jan - 29 Jan
The Appalachian at Mountain Creek
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 AED 577
AED 981 total
includes taxes & fees
25 Jan - 26 Jan
Villa Verde B&B, Greenwood Lake NY, 1
Dining

Hudson Valley Top Getaway with a River View B

Hudson Valley Top Getaway with a River View B
Newburgh
The price is AED 602
AED 1,167 total
includes taxes & fees
25 Jan - 26 Jan
Hudson Valley Top Getaway with a River View B
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.
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Top Middletown Hotel Reviews

Tru by Hilton Middletown

Tru by Hilton Middletown

10/10 Excellent
"Yes I enjoyed my stay"
Vivette 1-night trip
Posted 3 days ago
Tru by Hilton Middletown

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 43 accommodations. Though there aren't many apartments, we can help you locate accommodations with similar amenities. When you search on Expedia, you can use the filters to search for conveniences you might find in an apartment like a kitchen. You can also search for similar property types like condos, vacation homes, or cottages. 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 travelers who want to stay in at night and plan out their next day, but also for families wanting the conveniences of home.
What's a favorite apartment I should consider for a stay in Middletown?
Below is a favorite apartment to consider: Cottage Suites: Includes free WiFi. Free parking and onsite laundry facilities are on site.
What can I expect from the weather during my trip to 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 temp of 68°F, while the coldest months are January and February with an average of 31°F. The snowiest months in Middletown are January, February, March, and April, with each month seeing an average of 6 inches 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 Stewart Intl. Airport (SWF), which is located 17.8 mi (28.7 km) away from the heart of the city. If you'd like to venture out around the area, consider renting a car to take in more sights.

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