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Middletown Holiday Rentals

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Holiday Rentals in Middletown

Luxury Studio | Private kitchen
Cottage Suites
3.0 star property
The price is NZ$420
per night
28 May - 29 May
Cottage Suites
Property grounds
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (96)
"Comfortable apartment with a phenomenal view! The space could use a deep clean and some decluttering, but that view!!! Did I mention that the view was A-mazing?!?"
The price is NZ$433
per night
27 May - 28 May
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
1 bedroom, desk, iron/ironing board, travel cot
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
9.8 out of 10, Exceptional, (35)
"This is a cozy property in a very rural setting. The host is extremely responsive and very thorough. It is quiet and private. The furniture and bed are very comfortable. The wood burning stove is a pellet stove which provides enough heat to take the edge off. The hot tub could comfortably fit 4 people. The Village of Cold Spring is less than 10 minutes away, as is the Interstate 84 bridge across the Hudson. If you want to make your own food, bring it. There is no grocery store nearby."
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
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Property grounds
Lakefront Luxury on Greenwood Lake
10.0 out of 10, Exceptional, (115)
"We spent a much needed relaxing weekend at this location. I can't say enough good things about this property. It was beautifully decorated, perfectly supplied, and very clean. We would rent this property again."
Lakefront Luxury on Greenwood Lake
Exterior
Trails Head Cabin
9.8 out of 10, Exceptional, (57)
"This is a great property we have now stayed multiple times and the property owners make sure everything is perfect on arrival. Will be staying again!"
The price is NZ$342
per night
4 Jun - 5 Jun
Trails Head Cabin
Fireplace, books, music library, stereo
Lazy River Cottage on the Delaware River
10.0 out of 10, Exceptional, (119)
"The cottage was perfect! Everything about the cottage was just as it was described. The cottage was neat as a pin upon arrival, we got in at night and David had the light on and music playing for us. Would definitely recommend the Cottage to others as the perfect weekend retreat."
Lazy River Cottage on the Delaware River
Outdoor pool, a heated pool
Rustic Chic at Mountain Creek! Pool, Hot Tub, Sauna, Open ALL Year Round!
10.0 out of 10, Exceptional, (38)
"Great location: clean and comfy."
The price is NZ$415
per night
28 May - 29 May
Rustic Chic at Mountain Creek! Pool, Hot Tub, Sauna, Open ALL Year Round!
Property grounds
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
10.0 out of 10, Exceptional, (35)
"This sweet little apartment was perfect for my solo stay. Comfortable, quiet, and very easy to get to. Lovely view from the deck. It had a feeling of security and privacy. Vicky was quick with answering my emails."
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
Exterior
Trails Head Tiny House
10.0 out of 10, Exceptional, (5)
"It was great"
The price is NZ$203
per night
30 May - 31 May
Trails Head Tiny House
Property grounds
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
9.6 out of 10, Exceptional, (35)
"Three nights here as we toured the area. Check in was easy. We were able to access the VRBO app 30 minutes prior to our arrival. By the time we reached the driveway, Ruben had sent the access code.The road to the house is gravel and only wide enough for one car. We were glad we had arrived during the day.The house has an antique store vibe. Lots of books for a rainy day activity. FYI, the photos on the listing are a bit different from what we saw in the rooms. The dining table is larger with...
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
Fridge, microwave, oven, stovetop
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!
10.0 out of 10, Exceptional, (34)
"Thanks so much for a great stay. This is such a wonderful place for large groups! Nice hikes in the area too, which we took advantage of. Kitchen and bar area was especially good for cooking and eating for 30+ people!"
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!
Exterior
Serene Waterfront Log Cabin on 1 Wooded Acre with NEW REDUCED RATES FOR 2024!
9.8 out of 10, Exceptional, (156)
"Cabin was exactly as described. Very comfortable, great spot for my son and I and our two dogs. We had a great winter getaway, and hosts were very good communicators. I would gladly go back! Lots to do in the area..."
Serene Waterfront Log Cabin on 1 Wooded Acre with NEW REDUCED RATES FOR 2024!
Exterior
Cabin in the heart of the Hudson Valley, Cabin 4
8.4 out of 10, Very good, (11)
"Everything was as it says it was. Place was spotless. In the evening and morning you didn’t hear any traffic noise at all. Was quiet and peaceful. Communication with the property owner was outstanding."
The price is NZ$268
per night
4 Jun - 5 Jun
Cabin in the heart of the Hudson Valley, Cabin 4
Smart TV, fireplace
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
9.6 out of 10, Exceptional, (12)
"Great location and communication! Very clean and nice!"
The price is NZ$536
per night
27 May - 28 May
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
Property grounds
Renovated 1850's Cottage on Storm King Mountain
9.8 out of 10, Exceptional, (8)
"It was a beautiful setting with water fall. The home itself needs a little work. It is well used and needs some TLC. Photos look much better then actual home."
Renovated 1850's Cottage on Storm King Mountain
Property grounds
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
9.6 out of 10, Exceptional, (30)
"This place is wonderful!!!! It was a beautiful stay."
The price is NZ$614
per night
4 Jun - 5 Jun
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
Fridge, microwave, oven, stovetop
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!
6.4 out of 10, (5)
"This host is very irresponsible knowing 8 months in advanced about the reservation and not having the pool ready or even communicating that the pool would not be ready for use is just unexceptable. Also property has many things wrong with it. The oven doesn't work, the gas tank for the grill was left empty, all shower heads need to be replaced, the tv and mini Fridge in the basement bedroom dont work, the power outlet in the master bedroom doesn't work and the wall fixture above jacuzzi is just...
The price is NZ$1,584
per night
31 May - 1 Jun
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!
Fridge, microwave, oven, stovetop
Log Cabin in Catskill NYS
10.0 out of 10, Exceptional, (34)
"Was very clean, host was responsive and helpful. We had an issue with the gas and someone came to fix it within 2 hours. It snowed during our stay and the snow was plowed by someone twice. Could only find 2 bathrooms. Not a problem for our group, just informing. Overall, amazing stay and would recommend"
Log Cabin in Catskill NYS
Exterior
Cabin in the heart of the Hudson Valley, Cabin 2
9.4 out of 10, Exceptional, (3)
"Great tiny house for a stay upstate. Check in was easy and the place is clean!"
The price is NZ$268
per night
4 Jun - 5 Jun
Cabin in the heart of the Hudson Valley, Cabin 2
Lake
Fenced Yard Private Lakes 7 Beaches Huge Fire Pit
9.8 out of 10, Exceptional, (91)
"My family was down for the Spartan race weekend. The property is in a perfect location for proximity to the mountain, as well as Beaches and playgrounds for the kids. It comfortably fit four adults and two kids, and the fenced yard was great for the dog. Michael is a thoughtful and responsive owner, and we are looking forward to staying again next time we are down."
Fenced Yard Private Lakes 7 Beaches Huge Fire Pit
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See all available properties in Middletown
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.

Other types of properties in Middletown you may be interested in

Exterior
La Quinta Inn & Suites by Wyndham Middletown
2.5 star property
9.2 out of 10, Wonderful, (387)
"The staff was nice. Checking in was very quick and the place is clean. "
The price is NZ$245
per night
4 Jun - 5 Jun
La Quinta Inn & Suites by Wyndham Middletown
Reception
Tru by Hilton Middletown
2.5 star property
8.2 out of 10, Very good, (688)
"💪"
The price is NZ$238
per night
27 May - 28 May
Tru by Hilton Middletown
BBQ/picnic area
Sleep Inn & Suites Middletown - Goshen
2.5 star property
8.6 out of 10, Excellent, (850)
"Excellent!! "
The price is NZ$256
per night
10 Jun - 11 Jun
Sleep Inn & Suites Middletown - Goshen
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Middletown holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Middletown. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Middletown. Seeing all the best attractions is bound to make you fall in love with Middletown. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Middletown short-term rentals, that won’t be hard to do.

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?

Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits: This holiday home rental outside of Middletown is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Middletown?

With 17 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 Lakes State Park 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.

Recent reviews of Middletown properties
Expedia verified reviews