Photo by Vincent Ramundo

Middletown Holiday Rentals

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Holiday Rentals in Middletown

Luxury Studio | Private kitchen
Cottage Suites
3.0 star property
The price is AU$388
includes taxes & fees
17 May - 18 May
Cottage Suites
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 AU$366
includes taxes & fees
15 May - 16 May
Rustic Chic at Mountain Creek! Pool, Hot Tub, Sauna, Open ALL Year Round!
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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Exterior
Trails Head Cabin
9.8 out of 10, Exceptional, (56)
"We had a wonderful time, in spite of rain. The cabin was very comfortable and well stocked. It was literally less than a quarter of a mile to the hiking trails. Our dogs were very comfortable as well. One caveat. If you are coming in via RT. 209, do not turn off of Pine Kill Rd onto David Rhodes rd. Apparently GPS thinks you can go through, but it puts you on a dead end road. If you stay on Pine Kill, it will eventually route you the right way."
The price is AU$320
includes taxes & fees
16 May - 17 May
Trails Head Cabin
Property grounds
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
9.6 out of 10, Exceptional, (30)
"Family trip with teens and grandma. Beautiful home but unprepared for the gnats outside. Quiet location. Peaceful to sit outside around the fire pit. Kelly quickly responded to all questions and concerns. Kids enjoyed the ping pong table and grandma enjoyed the sunsets. Thank you for a great getaway!"
The price is AU$577
includes taxes & fees
16 May - 17 May
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
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!
Property grounds
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
10.0 out of 10, Exceptional, (34)
"Very nice property, immaculately clean and very close to the Riverside Art Venue. Both quiet and convenient for my time in Newburgh. I would definitely stay here again."
The price is AU$273
includes taxes & fees
27 May - 28 May
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 AU$191
includes taxes & fees
16 May - 17 May
Trails Head Tiny House
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
Located next to the Ski Resort, Bike Park and Water Park
10.0 out of 10, Exceptional, (143)
"Comfortable one bedroom condo. Pleasant and clean. Mountaintop ceremony was unique and beautiful."
Located next to the Ski Resort, Bike Park and Water Park
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 AU$250
includes taxes & fees
19 May - 20 May
Cabin in the heart of the Hudson Valley, Cabin 4
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 AU$406
includes taxes & fees
20 May - 21 May
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
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!
Fridge, microwave, oven, stovetop
Cozy family-friendly home!
10.0 out of 10, Exceptional, (3)
"Older manufactured home has been updated. We appreciated that each area had its own mini split unit for individual climate control. Area felt safe and quiet. Good hot water and water pressure. Kitchen was stocked for stovetop cooking but not much for baking, and no water glasses. (We just drank everything from the coffee cups.) Split bedroom layout was good for two couples. "
Cozy family-friendly home!
Fridge, microwave, oven, stovetop
Cozy country efficiency in the Hudson Valley
9.8 out of 10, Exceptional, (39)
"Quiet, clean and very comfortable. Beautiful property located just minutes from town. Will definitely stay here again."
The price is AU$332
includes taxes & fees
4 June - 5 June
Cozy country efficiency in the Hudson Valley
Smart TV, fireplace
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
9.6 out of 10, Exceptional, (11)
"The place was very clean and nice, but cable was out the whole weekend. Property management said they would send someone but never did."
The price is AU$500
includes taxes & fees
20 May - 21 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
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
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 AU$1,303
includes taxes & fees
16 May - 17 May
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!
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
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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, (379)
"Our stay was for 2 days we chose that hotel because it was pet friendly the rooms were ok I stayed in nicer hotels. The continental breakfast was average the sausages looked boiled etc not pleasant seen better"
The price is AU$226
includes taxes & fees
19 May - 20 May
La Quinta Inn & Suites by Wyndham Middletown
Reception
Tru by Hilton Middletown
2.5 star property
8.2 out of 10, Very good, (684)
"Staff at the desk was great "
The price is AU$204
includes taxes & fees
21 May - 22 May
Tru by Hilton Middletown
BBQ/picnic area
Sleep Inn & Suites Middletown - Goshen
2.5 star property
8.6 out of 10, Excellent, (844)
"The location is perfect and near family when we are visiting. I appreciate the breakfast options as well."
The price is AU$226
includes taxes & fees
20 May - 21 May
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.

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?

Trails Head Tiny House: This holiday home rental outside of Middletown is situated on a river, and has a BBQ and WiFi to help you feel content during your stay. Kitchen amenities include a stovetop, kitchenware and an electric kettle.

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.