Photo by Vincent Ramundo

Middletown Holiday 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
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Middletown

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 NZ$436
includes taxes & fees
16 Nov - 17 Nov
Cozy Haven: A Romantic Retreat in our Tiny House!

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!

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

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 NZ$537
includes taxes & fees
16 Nov - 17 Nov
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

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 NZ$543
includes taxes & fees
16 Nov - 17 Nov
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

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 NZ$311
includes taxes & fees
16 Nov - 17 Nov
Cabin in the heart of the Hudson Valley, Cabin 2

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 NZ$1,221
includes taxes & fees
14 Nov - 15 Nov
Large,Cozy,Bright Apartment, Business Themed.

Mountain Creek Resort Condo - Golf, Hike, Legoland, Bike, 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 NZ$469
includes taxes & fees
23 Nov - 24 Nov
Mountain Creek Resort Condo - Golf, Hike, Legoland, Bike, NYC 1 Hour

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

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

Milford
8.4 out of 10, Very good, (12)
"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 NZ$607
includes taxes & fees
20 Nov - 21 Nov
Lake front on glacial lake, swimming, boating, fishing. Floating dock

7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space

Monroe
6.8 out of 10, (5)
The price is NZ$2,012
includes taxes & fees
16 Nov - 17 Nov
7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space

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 NZ$493
includes taxes & fees
16 Nov - 17 Nov
Resort Getaway ! Mtn Creek Ski-In Ski-Out -Pool-Hot Tub-Sauna

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 NZ$749
includes taxes & fees
16 Nov - 17 Nov
Luxury 3 Br 2 Bath Condo With Steam Shower Ski Golf Relax

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

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

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 NZ$948
includes taxes & fees
16 Nov - 17 Nov
Modern penthouse suite in a restored grain tower with private roof deck.

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!

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 NZ$919
includes taxes & fees
16 Nov - 17 Nov
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

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 NZ$311
includes taxes & fees
23 Nov - 24 Nov
Cabin in the heart of the Hudson Valley, Cabin 4

Lux Lake Neepaulin Front Home

Wantage
8.0 out of 10, Very good, (2)
"Nice place to stay. "
United States
Bob
The price is NZ$483
includes taxes & fees
7 Dec - 8 Dec
Lux Lake Neepaulin Front Home
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Middletown Hotel Reviews

Find out more about Middletown

Everything you need to know about Middletown holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Middletown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middletown holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Middletown holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middletown. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middletown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middletown holiday rentals we have selected for you start as low as NZ$311 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Middletown rentals

At Expedia, we put the best Middletown holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Middletown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middletown holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middletown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 6 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 13 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?

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 such as LEGOLAND® New York and Woodbury Common Premium Outlets.

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.