Photo by Vincent Ramundo

Middletown Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • 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
Nov 28 - Nov 30
In two months
Jan 9 - Jan 11
In three months
Feb 6 - Feb 8
In four months
Mar 6 - Mar 8

Vacation Rentals in Middletown

TV, fireplace
Cozy Haven: A Romantic Retreat in our Tiny House!

Cozy Haven: A Romantic Retreat in our Tiny House!

Middletown
7.0 out of 10, Good, (9)
"I love the place but the cleanliness was bad, we found a condom under the bed and there was also blood on the bed sheets and a yellow stain on the bed. I’m sorry but for the price I expected something better than this."
United States
Jeferson Eleazar P.
The price is ￥16,876
￥37,695 total
includes taxes & fees
Nov 12 - Nov 13
Cozy Haven: A Romantic Retreat in our Tiny House!
6 bedrooms, desk, iron/ironing board, free WiFi
Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!

Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!

Monticello
9.0 out of 10, Wonderful, (86)
"Great property for a group trip. We enjoyed the house it was spacious and had everything we needed. The lake, kayaks and paddle boards were a lot of fun. I highly recommend and would stay again."
United States
Denise D.
Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!
Terrace/patio
Cove - King Bed Escape w/Hot Tub, Unit A

Cove - King Bed Escape w/Hot Tub, Unit A

Ellenville
10.0 out of 10, Exceptional, (2)
"The place was great, really enjoyed our stay! "
United States
Abby
Cove - King Bed Escape w/Hot Tub, Unit A
Smart TV, fireplace
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

Vernon Township
9.4 out of 10, Exceptional, (43)
"Really great place for an overnight trip to Mountain Creek. Plenty of space for 2 adults, great location and access to the amenities after a long day month slopes was a total bonus. Great communication, easy access and parking. "
United States
Eric M.
The price is ￥21,954
￥46,627 total
includes taxes & fees
Nov 14 - Nov 15
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
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, (126)
"I cannot say enough on this location. Peaceful, and the view was extraordinary. Highly recommend this to anyone that wants a getaway."
United States
Daniel R.
The price is ￥28,843
￥47,209 total
includes taxes & fees
Nov 24 - Nov 25
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Property grounds
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, (27)
"My partner and I stayed at the cabin for a writing retreat/getaway. It served us well and was perfect for our short trip. The host, Julie was very kind and helpful throughout our stay!"
United States
Thani B.
The price is ￥16,723
￥27,004 total
includes taxes & fees
Nov 24 - Nov 25
Cabin in the heart of the Hudson Valley, Cabin 2
Interior
Large,Cozy,Bright Apartment, Business Themed.

Large,Cozy,Bright Apartment, Business Themed.

Newburgh
9.0 out of 10, Wonderful, (15)
"Very cozy stay with responsive host"
United States
Adhith P.
The price is ￥66,277
￥104,750 total
includes taxes & fees
Nov 24 - Nov 25
Large,Cozy,Bright Apartment, Business Themed.
Property grounds
Mtn Creek Resort Condo - Mountain Bike, Hike, Golf, Swim, Legoland, NYC 1 Hour

Mtn Creek Resort Condo - Mountain Bike, Hike, Golf, Swim, Legoland, NYC 1 Hour

Vernon Township
10.0 out of 10, Exceptional, (53)
"Great Location and responsive owner. Thank you"
United States
Richard B.
The price is ￥16,787
￥40,898 total
includes taxes & fees
Nov 12 - Nov 13
Mtn Creek Resort Condo - Mountain Bike, Hike, Golf, Swim, Legoland, NYC 1 Hour
Outdoor dining
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

Newburgh
10.0 out of 10, Exceptional, (311)
"Beautiful location- owner was very responsive to any questions we had."
United States
Richard K.
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Exterior
Lake front on glacial lake, swimming, boating, fishing. Floating dock

Lake front on glacial lake, swimming, boating, fishing. Floating dock

Milford
8.2 out of 10, Very Good, (11)
"Over the weekend, we spent some time at George’s lakehouse, and it was truly beautiful. The view of the lake from the kitchen was breathtaking, and it was so easy to feel comfortable and relaxed there. We’re already looking forward to returning in the summer."
United States
Kyla H.
The price is ￥27,478
￥52,691 total
includes taxes & fees
Nov 20 - Nov 21
Lake front on glacial lake, swimming, boating, fishing. Floating dock
Property grounds
Resort Getaway ! Mtn Creek Ski-In Ski-Out -Pool-Hot Tub-Sauna

Resort Getaway ! Mtn Creek Ski-In Ski-Out -Pool-Hot Tub-Sauna

Vernon
10.0 out of 10, Exceptional, (70)
"It had an exciting and tranquil vibe and the friendly staff made the place even nicer. "
United States
Mary
The price is ￥20,672
￥43,031 total
includes taxes & fees
Nov 12 - Nov 13
Resort Getaway ! Mtn Creek Ski-In Ski-Out -Pool-Hot Tub-Sauna
Fridge, microwave, stovetop, dishwasher
Luxury 3 Br 2 Bath Condo With Steam Shower Ski Golf Relax

Luxury 3 Br 2 Bath Condo With Steam Shower Ski Golf Relax

Vernon
8.6 out of 10, Excellent, (91)
"Very pleasant."
United States
Margaret W.
The price is ￥24,279
￥65,382 total
includes taxes & fees
Nov 16 - Nov 17
Luxury 3 Br 2 Bath Condo With Steam Shower Ski Golf Relax
Fridge, microwave, oven, stovetop
Highland Group/Family Estate! 5 Private Units, Pool, Hotub, Gameroom; 40+ guests

Highland Group/Family Estate! 5 Private Units, Pool, Hotub, Gameroom; 40+ guests

2.0 star property
Monticello
8.0 out of 10, Very Good, (4)
"We had the BEST time staying here with our sorority sisters! The property is absolutely perfect for groups — so many private bedrooms that gave everyone their own space, plus the cutest houses and cabins that made it feel like a little village just for us. The dining hall was super chill and such a great hangout spot for meals and late-night laughs.We loved how close it was to everything — food, fun activities, and plenty of outdoor space to enjoy the yard. It made planning so easy since...
United States
Nancy D.
Highland Group/Family Estate! 5 Private Units, Pool, Hotub, Gameroom; 40+ guests
Terrace/patio
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

Newburgh
9.8 out of 10, Exceptional, (20)
"The house was beautiful inside and out. Owners were so nice and made sure we had everything we needed for our weekend getaway."
United States
Cindy B.
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9
Exterior
Walk to WP Gate + Free Parking!

Walk to WP Gate + Free Parking!

Highland Falls
9.8 out of 10, Exceptional, (19)
"Well equipped space and great communication from the host"
United States
Beth
The price is ￥27,523
￥47,940 total
includes taxes & fees
Nov 12 - Nov 13
Walk to WP Gate + Free Parking!
Exterior
Modern penthouse suite in a restored grain tower with private roof deck.

Modern penthouse suite in a restored grain tower with private roof deck.

Warwick
10.0 out of 10, Exceptional, (26)
"Wonderful stay!"
United States
Lisi M.
The price is ￥51,779
￥82,876 total
includes taxes & fees
Nov 12 - Nov 13
Modern penthouse suite in a restored grain tower with private roof deck.
Interior
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!

5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!

Monticello
9.6 out of 10, Exceptional, (49)
"The view was beautiful and the house was spotless. They had extra amenities that we forgot so we were set for our trip! Amazing owner who is very sweet and thoughtful!"
United States
Kayla U.
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!
Fridge, microwave, oven, stovetop
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

2.0 star property
New Paltz
9.4 out of 10, Exceptional, (24)
"Communication for check-in,checking out was flawless "
United States
tim m.
The price is ￥50,629
￥79,773 total
includes taxes & fees
Nov 16 - Nov 17
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
Outdoor dining
Cabin in the heart of the Hudson Valley, Cabin 4

Cabin in the heart of the Hudson Valley, Cabin 4

Newburgh
9.2 out of 10, Wonderful, (25)
"Great place to stay for a Beacon/Newburgh trip if you have a car, or like me, don’t mind hilly bike ride to and from. Cozy and affordable. "
United States
Derek L.
The price is ￥16,723
￥27,004 total
includes taxes & fees
Nov 24 - Nov 25
Cabin in the heart of the Hudson Valley, Cabin 4
Property grounds
3-bedroom house in charming Forestburgh with WiFi, AC. Start your getaway now.

3-bedroom house in charming Forestburgh with WiFi, AC. Start your getaway now.

Forestburgh
10.0 out of 10, Exceptional, (9)
"Lovely property in a serene and interesting setting. The hosts were so kind and communicative. We stayed for a night and enjoyed local sights and a concert in Bethel! "
United States
Erin
The price is ￥27,616
￥49,676 total
includes taxes & fees
Nov 12 - Nov 13
3-bedroom house in charming Forestburgh with WiFi, AC. Start your getaway now.
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
"clean rooms "
christine 1-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 vacation rental in Middletown?

Yes, we offer vacation rentals in Middletown close to Orange County Fairgrounds, or you can go with a more remote option if you'd like a relaxing place to 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 vacation home rentals that Middletown has to offer?

Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!: This vacation home rental outside of Middletown is located on a lake and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in Middletown?

With 13 Expedia vacation rentals, you're sure to find just the right place for your Middletown stay.

What’s there to see and do in Middletown?

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. While in the area, you can also visit popular places like LEGOLAND® New York and Woodbury Common Premium Outlets.

What’s a vacation rental in Middletown like?

Vacation rentals are privately owned properties you can book for short or long periods in Middletown. Vacation rentals offer extras such as hot tubs, fire pits, and patios so you'll have all the conveniences of home. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for a family getaway.