Middletown Holiday Rentals

  • 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
27 Feb - 1 Mar
In two months
10 Apr - 12 Apr
In three months
8 May - 10 May
In four months
5 Jun - 7 Jun

Our top choices for Middletown holiday rentals

Interior

Hello Small Stone

Hello Small Stone
Middletown
9.6 out of 10, Exceptional, (5 reviews)
"The house was great. It was nice to sit and relax by the small pond in the back."
United States
John H.
The price is HK$1,407
HK$3,404 total
includes taxes & fees
11 Mar - 12 Mar
Hello Small Stone
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$730
HK$1,473 total
includes taxes & fees
9 Mar - 10 Mar
Cozy 1-bedroom retreat minutes from West Point!
Interior

Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer

Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer
Beacon
10.0 out of 10, Exceptional, (47 reviews)
"Great place!"
United States
Sara B.
The price is HK$899
HK$1,944 total
includes taxes & fees
11 Mar - 12 Mar
Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer
Interior

Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks

Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
Kerhonkson
10.0 out of 10, Exceptional, (32 reviews)
"I love the place, very comfortable and cozy, Thank you so very much, Enjoyed a lot , Julia"
United States
Julia K.
The price is HK$814
HK$1,654 total
includes taxes & fees
15 Mar - 16 Mar
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
Living area

Cozy 2BR condo w/ valley views

Cozy 2BR condo w/ valley views
Vernon Township
9.6 out of 10, Exceptional, (24 reviews)
"Very nice stay really clean and beautiful views thanks a lot enjoyed snowboarding at creek for the 2 days "
United States
Jacqueline
The price is HK$852
HK$2,029 total
includes taxes & fees
11 Mar - 12 Mar
Cozy 2BR condo w/ valley views
1 bedroom, WiFi, bed sheets

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 HK$875
HK$1,863 total
includes taxes & fees
11 Mar - 12 Mar
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
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 HK$758
HK$2,134 total
includes taxes & fees
18 Feb - 19 Feb
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Fireplace, books

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Kerhonkson
9.4 out of 10, Exceptional, (12 reviews)
"Charming and relaxing cottage. Perfect location for hiking or enjoying Lake Minnewaska or Mohonk Preserve. "
United States
Patrick S.
The price is HK$1,083
HK$1,993 total
includes taxes & fees
26 Feb - 27 Feb
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Interior

Villa Verde B&B, bsm, Greenwood Lake NY

Villa Verde B&B, bsm, Greenwood Lake NY
Greenwood Lake
10.0 out of 10, Exceptional, (12 reviews)
"The breakfast was lovely!"
United States
Tara
The price is HK$1,227
HK$2,184 total
includes taxes & fees
11 Mar - 12 Mar
Villa Verde B&B, bsm, Greenwood Lake NY
Smart TV

Trails Head Cabin

Trails Head Cabin
Rock Hill
9.8 out of 10, Exceptional, (101 reviews)
"Really cozy stay I definitely have to come back during the summer months it was a beautiful experience !"
United States
Kimaya
The price is HK$767
HK$1,477 total
includes taxes & fees
15 Feb - 16 Feb
Trails Head Cabin
Interior

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

Luxe Loft on Main St.Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!
Warwick
10.0 out of 10, Exceptional, (42 reviews)
"This place was absolutely amazing. They have the nicest little studio I have ever rented. Perfect location, comfiest bed ever, awesome decor, and the coolest shower I have ever used in my life. I’d stay here again in a heartbeat. Truly was the perfect little place. "
United States
Patrick R.
The price is HK$860
HK$1,901 total
includes taxes & fees
18 Feb - 19 Feb
Luxe Loft on Main St.Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!
Smart TV

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Goshen
9.8 out of 10, Exceptional, (13 reviews)
"Beautiful location. We really enjoyed seeing the deer in the field every morning. "
United States
Aaron M.
The price is HK$1,161
HK$2,302 total
includes taxes & fees
24 Feb - 25 Feb
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Exterior

Cabin in the heart of the Hudson Valley, Cabin 2

Cabin in the heart of the Hudson Valley, Cabin 2
Newburgh
9.4 out of 10, Exceptional, (31 reviews)
"A very cute, convenient, and affordable stay with timely, friendly communication from the owner. Our dog loved it and we appreciated the ability to have a private place to stay."
United States
Sara B.
The price is HK$1,008
HK$1,560 total
includes taxes & fees
19 Feb - 20 Feb
Cabin in the heart of the Hudson Valley, Cabin 2
Interior

Lovely 3BR Home with parking-Walk to WP Gate!

Lovely 3BR Home with parking-Walk to WP Gate!
Highland Falls
10.0 out of 10, Exceptional, (7 reviews)
"Lovely home, great location and space for my family to have privacy. Enjoyed the deck for morning coffee. Would book again. "
United States
Briana T.
The price is HK$1,437
HK$2,759 total
includes taxes & fees
4 Mar - 5 Mar
Lovely 3BR Home with parking-Walk to WP Gate!
Interior

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Warwick
9.2 out of 10, Wonderful, (9 reviews)
"I really enjoyed my stay. The room was very clean, the inn is well located in town and it is great having the restaurant below. Would stay here again! "
United States
Erin R.
The price is HK$732
HK$1,252 total
includes taxes & fees
23 Feb - 24 Feb
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Property grounds

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (131 reviews)
"Amazing place Thanks for the stay "
United States
Julien C.
The price is HK$1,469
HK$2,378 total
includes taxes & fees
15 Feb - 16 Feb
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Exterior

Mountain View Retreat w/ Hot Tub, Theater, and Gym

Mountain View Retreat w/ Hot Tub, Theater, and Gym
Warwick
10.0 out of 10, Exceptional, (2 reviews)
"Amazing stay on a beautiful place!"
United States
Dorian G.
The price is HK$5,494
HK$10,009 total
includes taxes & fees
17 Feb - 18 Feb
Mountain View Retreat w/ Hot Tub, Theater, and Gym
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 HK$472
HK$1,312 total
includes taxes & fees
19 Feb - 20 Feb
Dream getaway apartment in the foot of Gunks Ridge
Pool

2 bedroom cozy condo with parking on premises

2 bedroom cozy condo with parking on premises
Vernon Township
10.0 out of 10, Exceptional, (34 reviews)
"The place was beautiful. Would highly recommended staying here. "
United States
Ranada
The price is HK$1,016
HK$2,311 total
includes taxes & fees
19 Feb - 20 Feb
2 bedroom cozy condo with parking on premises
Interior

Stylish & Pet-Friendly Apartment in Beacon

Stylish & Pet-Friendly Apartment in Beacon
Beacon
10.0 out of 10, Exceptional, (2 reviews)
"Very clean and great place to stay. "
United States
Charlene D.
The price is HK$1,243
HK$2,308 total
includes taxes & fees
15 Mar - 16 Mar
Stylish & Pet-Friendly Apartment in Beacon
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

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

10/10 Excellent
"Excellent"
Rosemarie 2-night trip
Posted 1 day ago
Sleep Inn & Suites Middletown - Goshen

Find out more about Middletown

Search for holiday rentals in Middletown on Expedia! You can easily find your home rentals, villas, holiday apartments in Middletown using one of the methods below:

  • View our selection of featured holiday rentals in Middletown
  • Use the map to find apartments and other holiday homes in the Middletown neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Middletown while they last

Look no further and take a look at our great range of rental properties in Middletown!

Frequently asked questions

Can I find a holiday rental in Middletown?

Yes, there are holiday rentals in Middletown close to Orange County Fairgrounds, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and shops in Middletown. Make sure you have time to check out the churches and architecture during your trip.

What are some of the best holiday rentals that Middletown has to offer?

Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!: This holiday home rental outside of Middletown is located on a lake, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Middletown?

With 11 Expedia holiday rentals, you're guaranteed to find just the right place for your Middletown stay.

What’s there to see and do in Middletown?

Thomas Bull Memorial Park and Highland Lake are a couple of scenic spots to enjoy the outdoors, whereas Paramount Theatre is one of the cultural attractions. Orange County Fair Speedway and Orange County Fairgrounds are other places to visit while you're in town.

What’s a holiday rental in Middletown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Middletown. Holiday rentals offer amenities such as hot tubs, fire pits and patios to help you enjoy your stay. If you're concerned about a sanitised environment, a holiday rental can provide a sense of security away from public hotel lifts and lobbies packed with people while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for family trips or small group gatherings.