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Middletown Holiday Rentals

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Holiday Rentals in Middletown

Charming bungalow in lovely Middletown NY
The price is AU$302
includes taxes & fees
17 Oct - 18 Oct
Charming bungalow in lovely Middletown NY
Hello Small Stone
9.6 out of 10, Exceptional, (5)
"The house was great. It was nice to sit and relax by the small pond in the back."
The price is AU$644
includes taxes & fees
19 Oct - 20 Oct
Hello Small Stone
Cozy Haven: A Romantic Retreat in our Tiny House!
7.0 out of 10, Good, (9)
"we enjoyed the cozy home it is a nice place to get away"
The price is AU$467
includes taxes & fees
19 Oct - 20 Oct
Cozy Haven: A Romantic Retreat in our Tiny House!
Arcabuco - upper camp Taino Woods, 15 minutes to Bethel Woods Concerts, Casino,
10.0 out of 10, Exceptional, (1)
"Taino wood was a great place for camping. Chantel and her husband Jesse are great host and are very welcoming and kind. Nice place to enjoy with your family in the nature. There were many tent sites inside their woods and we occupied the site called:Turey. We set up 3 tents (two 4-people tents and one 6-people tent). There was a firepit we used to cook food and Chantel and Jesse lend us a pot to cook. Before leaving Chantel, Jesse and a few of their friends sang indigenous songs and played...
The price is AU$135
includes taxes & fees
18 Oct - 19 Oct
Arcabuco - upper camp Taino Woods, 15 minutes to Bethel Woods Concerts, Casino,
Close to Trails: Studio w/ Water Views
3.0 star property
The price is AU$360
includes taxes & fees
30 Oct - 31 Oct
Close to Trails: Studio w/ Water Views
perfect studio, few minutes away to the heart of new Paltz & Mohonk Mountain
2.0 star property
The price is AU$439
includes taxes & fees
26 Oct - 27 Oct
perfect studio, few minutes away to the heart of new Paltz & Mohonk Mountain
Cozy 1-bedroom retreat minutes from West Point!
10.0 out of 10, Exceptional, (1)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
The price is AU$285
includes taxes & fees
21 Oct - 22 Oct
Cozy 1-bedroom retreat minutes from West Point!
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
10.0 out of 10, Exceptional, (31)
"This property paid attention to the details! There were clear instructions for everything including the wonderful steam shower and the washer/dryer and dishwasher. It was right in the heart of Beacon, and its location made it a great place to stay for day trips. Altogether, it was a great place to stay!"
The price is AU$377
includes taxes & fees
11 Nov - 12 Nov
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
Hike & Fish: Outdoor Retreat Near Trails
3.0 star property
The price is AU$470
includes taxes & fees
21 Oct - 22 Oct
Hike & Fish: Outdoor Retreat Near Trails
Serene lakeside oasis - fast WiFi 1.5 hrs from NYC, fire-pit & nature all around
9.4 out of 10, Exceptional, (11)
"A little off the beaten path, but a lovely Vrbo with excellent amenities with a nice natural surrounding."
The price is AU$437
includes taxes & fees
23 Oct - 24 Oct
Serene lakeside oasis - fast WiFi 1.5 hrs from NYC, fire-pit & nature all around
Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks
10.0 out of 10, Exceptional, (14)
"Can’t emphasize how nice the surrounding area and property itself are. Very relaxing while still being close to several small towns with great restaurants. Communication was excellent, overall a great experience! "
The price is AU$330
includes taxes & fees
5 Nov - 6 Nov
Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks
Cabin in the heart of the Hudson Valley, Cabin 3
9.8 out of 10, Exceptional, (13)
"We had a great stay, everything you need is provided. Would recommend to anyone."
The price is AU$370
includes taxes & fees
21 Oct - 22 Oct
Cabin in the heart of the Hudson Valley, Cabin 3
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
9.8 out of 10, Exceptional, (41)
"Adorable place to stay in an adorable town! "
The price is AU$366
includes taxes & fees
11 Nov - 12 Nov
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
Cozy Loft Cabin high above Bashakill Wildlife Refuge
9.4 out of 10, Exceptional, (25)
"A fantastic little getaway after a wonderful day of hiking the Catskills! Vinny & Josh were perfect hosts and the property is fantastic! Will definitely be back! "
The price is AU$296
includes taxes & fees
20 Oct - 21 Oct
Cozy Loft Cabin high above Bashakill Wildlife Refuge
Cozy 1-bedroom condo-Ski in/out/Waterpark/King Bed/WIFI/Parking
2.5 star property
9.2 out of 10, Wonderful, (5)
"We stayed in this unit and absolutely loved it. We were just a short drive away from the all the orchards in Warwick, NY. The accommodations were perfectly located with quite a few things to do in the area. We will stay again. "
The price is AU$389
includes taxes & fees
13 Nov - 14 Nov
Cozy 1-bedroom condo-Ski in/out/Waterpark/King Bed/WIFI/Parking
Luxe Loft on Main St.- Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!
10.0 out of 10, Exceptional, (35)
"The property was as advertised. The location is great. We felt supported in our stay. "
The price is AU$390
includes taxes & fees
16 Nov - 17 Nov
Luxe Loft on Main St.- Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
9.8 out of 10, Exceptional, (11)
"Wonderful cottage - lots of natural light - well equipped - great shower- comfortable beds- near Legoland - affordable- beautiful surroundings with great sunsets and sunrises - "
The price is AU$446
includes taxes & fees
26 Oct - 27 Oct
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
2 Lake Cabins Pool+hottub Game Room 23acs
2.0 star property
2 Lake Cabins Pool+hottub Game Room 23acs
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
9.0 out of 10, Wonderful, (6)
"Nice to have top notch bar/restaurant downstairs!"
The price is AU$239
includes taxes & fees
20 Oct - 21 Oct
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Grant - A Tranquil One Bedroom Steps from River
9.6 out of 10, Exceptional, (35)
"Stan is really nice and helpful. The apartment is really well designed, spacious and clean, very well equipped with a nice porch. Stan is really thoughtful. Recommended!"
The price is AU$406
includes taxes & fees
21 Oct - 22 Oct
Grant - A Tranquil One Bedroom Steps from River
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$194 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 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 12 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.