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Middletown Holiday Rentals

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Holiday Rentals in Middletown

Cozy Haven: A Romantic Retreat in our Tiny House!

Middletown
6.8 out of 10, (11)
"we enjoyed the cozy home it is a nice place to get away"
United States
Yidel
Cozy Haven: A Romantic Retreat in our Tiny House!

Charming bungalow in lovely Middletown NY

Middletown
The price is AU$301
includes taxes & fees
1 Dec - 2 Dec
Charming bungalow in lovely Middletown NY

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

Monticello
9.0 out of 10, Wonderful, (87)
"This is a perfect place for a large group to stay and not get bored! Lots of space inside and out. Super clean, and well maintained. The host replied to my messages super quick! Totally recommend this property!"
United States
Anonymous traveller
Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!

Luxe Retreat with Fireplace/WiFi/Pool near Water Parks, Golf Course, Wineries

2.0 star property
Vernon
10.0 out of 10, Exceptional, (5)
"Cozy property with privacy and comfort. "
United States
Anonymous traveller
Luxe Retreat with Fireplace/WiFi/Pool near Water Parks, Golf Course, Wineries

Lake Glenwood A-Frame Cabin stunning views, fire pit, game room, Pet Friendly

Sussex
10.0 out of 10, Exceptional, (35)
"Wonderful place and cozy will book again "
United States
Alex P.
The price is AU$1,031
includes taxes & fees
26 Dec - 27 Dec
Lake Glenwood A-Frame Cabin stunning views, fire pit, game room, Pet Friendly

Trails Head Cabin

Rock Hill
9.8 out of 10, Exceptional, (95)
"Great location that's super close to the trailhead, very convenient for those that want to hike in the area! Very easy check-in and reasonably priced. My partner and I had a wonderful time staying here."
United States
Qiuwei Z.
The price is AU$335
includes taxes & fees
1 Dec - 2 Dec
Trails Head Cabin

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 AU$1,066
includes taxes & fees
1 Dec - 2 Dec
Large,Cozy,Bright Apartment, Business Themed.

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

Vernon Township
9.4 out of 10, Exceptional, (43)
"Was there for a 2 night stay and everything was perfect!"
United States
Bob W.
The price is AU$469
includes taxes & fees
7 Dec - 8 Dec
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

2 bedroom cozy condo with parking on premises

Vernon Township
10.0 out of 10, Exceptional, (31)
"The place was beautiful. Would highly recommended staying here. "
United States
Ranada
The price is AU$456
includes taxes & fees
23 Dec - 24 Dec
2 bedroom cozy condo with parking on premises

Lazy River Cottage on the Delaware River

Matamoras
10.0 out of 10, Exceptional, (164)
"Amazing stay "
United States
M S.
Lazy River Cottage on the Delaware River

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

Monroe
6.8 out of 10, (5)
"It was a great home with lots of space indoor and outside. "
United States
Yogita R.
7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space

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

Cabin in the heart of the Hudson Valley, Cabin 2

Newburgh
9.4 out of 10, Exceptional, (29)
"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 AU$308
includes taxes & fees
1 Dec - 2 Dec
Cabin in the heart of the Hudson Valley, Cabin 2

TRANQUIL MOUNTAIN SOLITUDE

Pine Bush
10.0 out of 10, Exceptional, (4)
"Such a quaint & cozy little hideaway! Hosts could not be more hospitable. Thank you for a great stay!"
United States
Michelle H.
The price is AU$343
includes taxes & fees
2 Dec - 3 Dec
TRANQUIL MOUNTAIN SOLITUDE

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

Monticello
9.6 out of 10, Exceptional, (50)
"Amazing spot in the Catskills! Plenty of beds and rooms."
United States
Taurance R.
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Fort Montgomery
9.8 out of 10, Exceptional, (129)
"It has an incredible mountain and water view. "
United States
MIHYUN
The price is AU$475
includes taxes & fees
1 Dec - 2 Dec
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Luxurious Ski in-Ski Out Mnt. Creek/Hot tub/Tennis & Pickleball/Heated pool/Golf

Vernon
9.8 out of 10, Exceptional, (88)
"House is fantastic. We have stayed here for three years in a row so that should tell you everything you need to know. "
United States
Michael C.
Luxurious Ski in-Ski Out Mnt. Creek/Hot tub/Tennis & Pickleball/Heated pool/Golf

Luxury 9BR Retreat w/Pool & Hot Tub

Chester
7.0 out of 10, Good, (2)
"Pool was not open or usable but we were not interested in doing that "
United States
John D.
Luxury 9BR Retreat w/Pool & Hot Tub

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

Newburgh
9.8 out of 10, Exceptional, (20)
"Great host, amazing area, perfect get away!"
United States
Gianna W.
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

Our home is perfect for relaxing and having lots of fun, with near by activity’s

Highland
9.4 out of 10, Exceptional, (10)
"Enjoyed the stay. Nice place to relax for a weekend."
United States
Marie J.
Our home is perfect for relaxing and having lots of fun, with near by activity’s
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

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 favourite 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 depend 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 AU$301 per night. Entering your travel dates in the search wizard might find you 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 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 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. 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.