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Middletown Vacation Rentals

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Check prices for these dates

Tonight
Jan 31 - Feb 1
Tomorrow
Feb 1 - Feb 2
This weekend
Jan 31 - Feb 2
Next weekend
Feb 7 - Feb 9

Vacation Rentals in Middletown

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Property grounds

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (106)
"Great place and host!"
The price is CA $242
CA $354 total
includes taxes & fees
Feb 4 - Feb 5
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Greenwoods of Warwick
Fridge, microwave, oven, stovetop

Greenwoods of Warwick

9.8 out of 10, Exceptional, (8)
"Home was very clean. The host was very friendly & informative. The beds were very comfortable. We would highly recommend staying at this location. We will definitely stay here again. 👍 "
Greenwoods of Warwick
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
Smart TV, fireplace

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

9.6 out of 10, Exceptional, (23)
"Great place for family ski vacation. Apt was clean, with amenities for cooking. Great fireplace. The ski areas are very kid friendly. The bunny slope was carved up into different trails for learning different skills. Didn’t need to drive to get things. Everything for a great stay was right on site."
The price is CA $230
CA $470 total
includes taxes & fees
Feb 3 - Feb 4
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!
Fridge, microwave, oven, stovetop

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

9.6 out of 10, Exceptional, (38)
"The whole family had a great time! We would love to come back!"
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!
Luxury River-View House w/ Hot Tub & Hiking Trails | By Dream House in the Gunks
Fridge, microwave, oven, stovetop

Luxury River-View House w/ Hot Tub & Hiking Trails | By Dream House in the Gunks

2.0 star property
10.0 out of 10, Exceptional, (1)
"My husband and I had an amazing time. Absolutely beautiful home, great location, and overall amazing experience. "
The price is CA $402
CA $644 total
includes taxes & fees
Feb 4 - Feb 5
Luxury River-View House w/ Hot Tub & Hiking Trails | By Dream House in the Gunks
Luxury 3 Br 2 Bath Condo With Steam Shower Ski Golf Relax
Fridge, microwave, stovetop, dishwasher

Luxury 3 Br 2 Bath Condo With Steam Shower Ski Golf Relax

9.0 out of 10, Wonderful, (75)
"We enjoyed our stay at this condo. There was plenty of space for us to hang out and sleep. We used the kitchen a lot and for the most part it was well equipped. We could have used more things like larger bowls to mix things or for chips. The downstairs bathroom shower could also use a curtain so that the water doesn’t get everywhere. The condo was easy to find and check in. The owner reached out to make sure we were good which was nice. Overall our family was happy with the unit "
The price is CA $252
CA $643 total
includes taxes & fees
Feb 2 - Feb 3
Luxury 3 Br 2 Bath Condo With Steam Shower Ski Golf Relax
Trails Head Cabin
Exterior

Trails Head Cabin

9.8 out of 10, Exceptional, (75)
"This is the perfect getaway to reconnect with a partner or family. Very peaceful, cozy and beautiful scenery. Also great place to stay in and cook as well. Simple getaway you can’t beat!"
The price is CA $180
CA $295 total
includes taxes & fees
Feb 3 - Feb 4
Trails Head Cabin
Luxurious 7 Bedroom Estate with Heated Pool and Hot Tub
Fridge, microwave, oven, stovetop

Luxurious 7 Bedroom Estate with Heated Pool and Hot Tub

Luxurious 7 Bedroom Estate with Heated Pool and Hot Tub
Spacious Getaway! 7BR w Park & pool Scenic Views
Smart TV, fireplace, computer monitors

Spacious Getaway! 7BR w Park & pool Scenic Views

Spacious Getaway! 7BR w Park & pool Scenic Views
Amazing Villa! Indoor Hotub 🌟🌟🌟🌟🌟, Heated Pool, Game Room -Sleeps 25+ Ski
Indoor pool, outdoor pool

Amazing Villa! Indoor Hotub 🌟🌟🌟🌟🌟, Heated Pool, Game Room -Sleeps 25+ Ski

9.6 out of 10, Exceptional, (20)
"Our stay was great! Host was great at communicating. Enough towels were supplied. Beds were very comfortable. Highly recommended!"
Amazing Villa! Indoor Hotub 🌟🌟🌟🌟🌟, Heated Pool, Game Room -Sleeps 25+ Ski
Lazy River Cottage on the Delaware River
Fireplace, books, music library, stereo

Lazy River Cottage on the Delaware River

10.0 out of 10, Exceptional, (136)
"what a lovely lovely cottage by the lake very clean all the amenities inside the house. Contact with the host was amazing. Fire pit fireplace very lovely place. Will stay there again."
Lazy River Cottage on the Delaware River
Kick back & relax in this peaceful, stylish place to stay with the whole family.
Fridge, microwave, oven, stovetop

Kick back & relax in this peaceful, stylish place to stay with the whole family.

10.0 out of 10, Exceptional, (22)
"Our family went to the Hudson Valley area for a wedding. Pre stay communication with Malka was excellent and we all had a wonderful time. Lots of room for the kids to play and be entertained downstairs as well as upstairs in the Projection Room. The backyard was a great soccer area and the fire pit was great to sit around at night. Firewood on site was a real plus! I do recommend to anyone doing substantial cooking for many people to bring their own favorite pots and pans if possible though...
Kick back & relax in this peaceful, stylish place to stay with the whole family.
2 bedroom cozy condo with parking on premises
Fridge, microwave, oven, stovetop

2 bedroom cozy condo with parking on premises

10.0 out of 10, Exceptional, (21)
"My husband and I were attending the Halloween event and rented this property. It was very clean and cozy. I highly recommend. My only issue was that you have to check out by 11 am. I personally feel it was too early. I requested if I can check out at 12pm but, it was a no. Not a big deal but after going to a party we could’ve used an extra 2 hour sleep. All in all I would rent again. "
The price is CA $187
CA $426 total
includes taxes & fees
Feb 4 - Feb 5
2 bedroom cozy condo with parking on premises
BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.
Miscellaneous

BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.

10.0 out of 10, Exceptional, (1)
"Alexis was a great host and she was super communicative and easy to reach. The house was clean and prefect size for my group of 6. Most things were stocked but I’d reach out to the host in advance so you can buy anything that isn’t ahead of time. One important thing to note is that the driveway can only fit 2 cars and there isn’t really any street parking. "
BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.
Hiking/Climbing Paradise- walking distance to Mohonk/Gunks/Minnewaska
Property grounds

Hiking/Climbing Paradise- walking distance to Mohonk/Gunks/Minnewaska

9.8 out of 10, Exceptional, (92)
"This property was spectacular. Immaculately clean and every detail done well. From a fully stocked and ready to go kitchen, to comfortable beds, sheets and towels. I’ll be back to stay here again and the host Michelle couldn’t have done more. Having had a few disappointing stays in other properties of late, this was a welcome game changer!!!"
Hiking/Climbing Paradise- walking distance to Mohonk/Gunks/Minnewaska
Vernon Condo w/ Deck, Near Appalachian Trail!
Property grounds

Vernon Condo w/ Deck, Near Appalachian Trail!

7.6 out of 10, Good, (29)
"This was our 2nd time staying at this condo. It’s perfect for our families. Convenient to Mountain Creek to ski all day and night while taking breaks back at the condo. We will be coming back as we know the cleanliness, size of the condo and location is perfect. If having a larger group definitely reach out to book the top unit as well. "
Vernon Condo w/ Deck, Near Appalachian Trail!
Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons
Living area

Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons

2.0 star property
9.0 out of 10, Wonderful, (4)
"Just what we needed with lots of space very clean and comfortable"
Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons
Mountain View escape
Exterior

Mountain View escape

10.0 out of 10, Exceptional, (46)
"Can’t wait to go back, if I could move this home to Myrtle Beach I would. Fantastic communication with homeowner, great location. Homeowner keeps the home stocked with goodies, extra plus! Very cozy and Quiet it’s a 10 Star "
Mountain View escape
Entire Lakehouse Cabin by Mountain Creek & Warwick
Fridge, microwave, oven, stovetop

Entire Lakehouse Cabin by Mountain Creek & Warwick

10.0 out of 10, Exceptional, (109)
"Home was clean, well stocked, and had a very cozy feel. Cat was a pleasure to communicate with and very thorough in every aspect of the rental instructions. Everything was supplied from firewood to bath essentials and everything in between.We thoroughly enjoyed our stay and would rent again in the future."
Entire Lakehouse Cabin by Mountain Creek & Warwick
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!
Fridge, microwave, oven, stovetop

Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!

7.0 out of 10, Good, (15)
"This home was just what our group of 16 needed to find rest, reconvene from the day’s activities, and prepare for all the next day’s activities. The town of Monroe was a great place to stay as it was centrally located for all the places we visited. "
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!
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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Other types of properties in Middletown you may be interested in

Courtyard by Marriott Middletown Goshen
Property amenity

Courtyard by Marriott Middletown Goshen

3.0 star property
8.6 out of 10, Excellent, (827)
"Overall great service "
The price is CA $130
CA $153 total
includes taxes & fees
Feb 6 - Feb 7
Courtyard by Marriott Middletown Goshen
Hampton Inn by Hilton Middletown
Exterior

Hampton Inn by Hilton Middletown

2.5 star property
8.6 out of 10, Excellent, (1001)
"I was a little afraid of the bath tub as it was slippery with no mat. Otherwise all was well."
The price is CA $122
CA $144 total
includes taxes & fees
Feb 13 - Feb 14
Hampton Inn by Hilton Middletown
Sleep Inn & Suites Middletown - Goshen
BBQ/picnic area

Sleep Inn & Suites Middletown - Goshen

2.5 star property
8.6 out of 10, Excellent, (1003)
"Everything was fine, except i had trouble with the thermostat & raising the temperature in my room. "
The price is CA $123
CA $139 total
includes taxes & fees
Feb 16 - Feb 17
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 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?

5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!: 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 9 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 patio, a private yard, 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 Highland Lakes State 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 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.