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Middletown Vacation Rentals

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Vacation Rentals in Middletown

Exterior
Hello Small Stone
Hello Small Stone
9.6 out of 10, Exceptional, (5)
"The house has a lot of character and the outdoor areas are really peaceful. The owner just needs to resolve the issue with sulfur in the water because the rotten egg smell is too strong to tolerate."
United States
David
$389 nightly
The price is $440
Nov 13 - Nov 14
Total with taxes and fees
Hello Small Stone
Interior
Charming bungalow in lovely Middletown NY
Charming bungalow in lovely Middletown NY
$165 nightly
The price is $195
Nov 7 - Nov 8
Total with taxes and fees
Charming bungalow in lovely Middletown NY
TV, fireplace
Cozy Haven: A Romantic Retreat in our Tiny House!
Cozy Haven: A Romantic Retreat in our Tiny House!
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.
$254 nightly
The price is $300
Nov 9 - Nov 10
Total with taxes and fees
Cozy Haven: A Romantic Retreat in our Tiny House!
Property grounds
Arcabuco - upper camp Taino Woods, 15 minutes to Bethel Woods Concerts, Casino,
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...
United States
Lissette
$95 nightly
The price is $106
Nov 7 - Nov 8
Total with taxes and fees
Arcabuco - upper camp Taino Woods, 15 minutes to Bethel Woods Concerts, Casino,
Fridge, oven, stovetop, cookware/dishes/utensils
Cozy 1-bedroom retreat minutes from West Point!
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!) "
United States
Zack C.
$175 nightly
The price is $191
Nov 17 - Nov 18
Total with taxes and fees
Cozy 1-bedroom retreat minutes from West Point!
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
9.0 out of 10, Wonderful, (6)
"Although the original check-in process was fine, the host became unresponsive to our questions during the stay. We were able to figure out the answers to our questions, but it would have been nice to hear anything at all. We went so far as to text the host because we became concerned after radio silence for 3 days. Once she did respond she didn't apologize for not getting back to us and ghosting us for days. "
United States
Patty M.
$131 nightly
The price is $148
Nov 9 - Nov 10
Total with taxes and fees
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Terrace/patio
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
2.0 star property
10.0 out of 10, Exceptional, (7)
"Absolutely worth it, this place is a great getaway in a dreamy spot in the woods, with everything you need to relax. Don’t forget to turn on the heated floors and hook up your tunes to the bathroom Bluetooth speaker. Thanks for a wonderful experience! "
United States
Samantha
$281 nightly
The price is $285
Nov 11 - Nov 12
Total with taxes and fees
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
Property grounds
Cozy 1-bedroom condo-Ski in/out/Waterpark/King Bed/WIFI/Parking
Cozy 1-bedroom condo-Ski in/out/Waterpark/King Bed/WIFI/Parking
2.5 star property
9.4 out of 10, Exceptional, (6)
"This was my family’s first Vrbo experience and we couldn’t be more happy with the property! The owner, Henry, was very quick to respond when we needed a little guidance on to check in and also made sure to check in with me later on to see if we settled in ok. The property was super cute and quaint for our snowboarding trip. We cannot wait to come back again! "
United States
Samantha
$209 nightly
The price is $236
Nov 9 - Nov 10
Total with taxes and fees
Cozy 1-bedroom condo-Ski in/out/Waterpark/King Bed/WIFI/Parking
Interior
Dream House in the Gunks
Dream House in the Gunks
10.0 out of 10, Exceptional, (32)
"I love the place, very comfortable and cozy, Thank you so very much, Enjoyed a lot , Julia"
United States
Julia K.
$219 nightly
The price is $222
Nov 12 - Nov 13
Total with taxes and fees
Dream House in the Gunks
Fridge, microwave, oven, stovetop
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
10.0 out of 10, Exceptional, (44)
"Great location, so clean and comfortable. "
United States
Barbara
$211 nightly
The price is $243
Nov 20 - Nov 21
Total with taxes and fees
Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer
Property grounds
Charming house with brook in the picturesque Village of Wurtsboro min from shops
Charming house with brook in the picturesque Village of Wurtsboro min from shops
Charming house with brook in the picturesque Village of Wurtsboro min from shops
Exterior
Trails Head Tiny House
Trails Head Tiny House
9.0 out of 10, Wonderful, (19)
"A wonderful place out of everything and at the same time close to the city. Very calm place. Brittani, the host, was fantastic since the reserve day."
United States
Brenda A.
$111 nightly
The price is $125
Nov 9 - Nov 10
Total with taxes and fees
Trails Head Tiny House
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
9.8 out of 10, Exceptional, (42)
"Adorable place to stay in an adorable town! "
United States
Mary L.
$205 nightly
The price is $236
Nov 11 - Nov 12
Total with taxes and fees
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
Outdoor spa tub
Guest Suite 2-bedrooms with AC, Hot Tub and WiFi in peaceful Matamoras,
Guest Suite 2-bedrooms with AC, Hot Tub and WiFi in peaceful Matamoras,
2.0 star property
9.2 out of 10, Wonderful, (5)
"An immaculately clean, comfortable and quiet house with spacious rooms and comfortable furnishings. The owners were super friendly and responsive to our needs. We hope to stay here again next year."
United States
Denise
$252 nightly
The price is $274
Nov 11 - Nov 12
Total with taxes and fees
Guest Suite 2-bedrooms with AC, Hot Tub and WiFi in peaceful Matamoras,
Terrace/patio
Dream getaway apartment in the foot of Gunks Ridge
Dream getaway apartment in the foot of Gunks Ridge
9.6 out of 10, Exceptional, (24)
"This was such a great option for us as we were only in town for the night for a haunted house attraction. The space is extremely spacious, very nicely decorated and gave us the fall season feeling. A great stay and would definitely do it again!"
United States
Crystal L.
$181 nightly
The price is $184
Nov 9 - Nov 10
Total with taxes and fees
Dream getaway apartment in the foot of Gunks Ridge
Private kitchen
Treeview - Cozy 2 BR Apartment - Fast WiFi ~ 1 hr from NYC - 5 mins to downtown
Treeview - Cozy 2 BR Apartment - Fast WiFi ~ 1 hr from NYC - 5 mins to downtown
10.0 out of 10, Exceptional, (4)
"Full kitchen, lovely bathroom. Enjoyed my stay for 2 nights. Very near main restaurant/cafe area of Port Jervis. Described as is. Provided detailed instructions for entry and stay. Good communication."
United States
Diane & Terry W.
$266 nightly
The price is $314
Nov 12 - Nov 13
Total with taxes and fees
Treeview - Cozy 2 BR Apartment - Fast WiFi ~ 1 hr from NYC - 5 mins to downtown
Dining
Serene Rustic Retreat with Lake
Serene Rustic Retreat with Lake
2.0 star property
10.0 out of 10, Exceptional, (8)
"We had the best weekend at Westly's house. It was better then the pictures. So much room for us to relax. We will come back again. Giving 5 stars perfect. "
United States
Anonymous traveler
$474 nightly
The price is $481
Nov 7 - Nov 8
Total with taxes and fees
Serene Rustic Retreat with Lake
Interior
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
9.2 out of 10, Wonderful, (5)
"My girlfriend and I loved our stay here! We stayed for one night and it was perfect for what we needed. Very clean with easy self-check-in. The host was very responsive with all inquiries. Short walk to nice downtown area as well!"
United States
Jay D.
$133 nightly
The price is $150
Nov 9 - Nov 10
Total with taxes and fees
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
Exterior
Trails Head Cabin
Trails Head Cabin
9.8 out of 10, Exceptional, (94)
"We arrived and the check-in process was a simple as it gets. Step inside and it's a cute little cabin that was roomy and clean! The property has an outdoor space and was sooooooo quiet which was exactly what we were looking for."
United States
Bill M.
$180 nightly
The price is $202
Nov 9 - Nov 10
Total with taxes and fees
Trails Head Cabin
House (1 Bedroom) | Interior
Hike & Fish: Outdoor Retreat Near Trails
Hike & Fish: Outdoor Retreat Near Trails
3.0 star property
$271 nightly
The price is $306
Nov 9 - Nov 10
Total with taxes and fees
Hike & Fish: Outdoor Retreat Near Trails
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

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

10/10 Excellent
"Enjoyed my stay the rooms were very clean and nice "
Paige 2-night trip
Posted 19 hours ago
Sleep Inn & Suites Middletown - Goshen

Find out more about Middletown

Everything you need to know about Middletown vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Middletown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middletown vacation 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 low season months. For more hustle and bustle, you may prefer to visit Middletown in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $176 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Middletown rentals

At Expedia, we put the best Middletown vacation 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 vacation.

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.

Explore a world of travel with Expedia

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.