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Middletown Vacation Rentals

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Check prices for these dates

Tonight
Sep 26 - Sep 27
Tomorrow
Sep 27 - Sep 28
This weekend
Sep 26 - Sep 28
Next weekend
Oct 3 - Oct 5

Vacation Rentals in Middletown

Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!
6 bedrooms, desk, iron/ironing board, free WiFi

Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!

9.0 out of 10, Wonderful, (83)
"Great property for a group trip. We enjoyed the house it was spacious and had everything we needed. The lake, kayaks and paddle boards were a lot of fun. I highly recommend and would stay again."
Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!
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, (122)
"It has an incredible mountain and water view. "
The price is ￥28,153
￥46,080 total
includes taxes & fees
Sep 30 - Oct 1
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
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

9.4 out of 10, Exceptional, (38)
"Very nice condo, had everything we needed. Included a parking pass, gym pass and pool pass. Super clean. Thanks for having us!"
The price is ￥21,296
￥44,783 total
includes taxes & fees
Oct 3 - Oct 4
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick
Interior

Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick

9.8 out of 10, Exceptional, (12)
"This property has exactly what we were looking for to spend a long weekend and create new memories. The welcoming atmosphere and breathtaking views offer a unique experience. Jones was easily accessible to respond to any questions. We will certainly come and definitely recommend this property to family and friends. "
Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Outdoor spa tub

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

10.0 out of 10, Exceptional, (22)
"Clean, comfortable, beautiful views, cute little town. Super accommodating host. Couldn’t have asked for more. "
The price is ￥30,324
￥75,980 total
includes taxes & fees
Oct 1 - Oct 2
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Outdoor dining

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

10.0 out of 10, Exceptional, (308)
"Fortunate to have found the time to spend a long weekend by the lake. Just the right remedy for our usual fast-paced schedules. Caught a beautiful sunset the first evening but every day was just as enjoyable."
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Mtn Creek Resort Condo - Mountain Bike, Hike, Golf, Swim, Legoland, NYC 1 Hour
Property grounds

Mtn Creek Resort Condo - Mountain Bike, Hike, Golf, Swim, Legoland, NYC 1 Hour

10.0 out of 10, Exceptional, (50)
"Excelente place to stay and the host was very attentive.Will definitely be back "
The price is ￥16,308
￥40,180 total
includes taxes & fees
Sep 28 - Sep 29
Mtn Creek Resort Condo - Mountain Bike, Hike, Golf, Swim, Legoland, NYC 1 Hour
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
Fridge, microwave, oven, stovetop

Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

2.0 star property
9.8 out of 10, Exceptional, (17)
"The property was perfectly secluded while being close to town. We observed lots of wildlife including deer, a woodchuck family, and a turtle laying eggs! The house was roomy and comfortable with just enough upscale elegance that made us feel pampered."
The price is ￥56,755
￥82,117 total
includes taxes & fees
Sep 29 - Sep 30
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
Condo at Mtn Creek 1 Bdr 1 Bath sleep 4 Mtn view #234
Outdoor pool, a heated pool

Condo at Mtn Creek 1 Bdr 1 Bath sleep 4 Mtn view #234

10.0 out of 10, Exceptional, (4)
"This property was comfortable, quaint and clean. Perfect little weekend getaway. We definitely plan on staying here again. "
The price is ￥16,473
￥37,216 total
includes taxes & fees
Sep 29 - Sep 30
Condo at Mtn Creek 1 Bdr 1 Bath sleep 4 Mtn view #234
3-bedroom house in charming Forestburgh with WiFi, AC. Start your getaway now.
Property grounds

3-bedroom house in charming Forestburgh with WiFi, AC. Start your getaway now.

10.0 out of 10, Exceptional, (9)
"Lovely property in a serene and interesting setting. The hosts were so kind and communicative. We stayed for a night and enjoyed local sights and a concert in Bethel! "
The price is ￥26,788
￥47,865 total
includes taxes & fees
Oct 4 - Oct 5
3-bedroom house in charming Forestburgh with WiFi, AC. Start your getaway now.
Luxurious Ski in-Ski Out Mnt. Creek/Hot tub/Tennis & Pickleball/Heated pool/Golf
Outdoor pool, a heated pool

Luxurious Ski in-Ski Out Mnt. Creek/Hot tub/Tennis & Pickleball/Heated pool/Golf

9.8 out of 10, Exceptional, (86)
"Such a magical property! I came here with some friends for my birthday weekend and we had the most incredible time. The space- both indoors and out, is even more beautiful than the pictures (which never happens!). Everything was very clean and well kept. And the property manager was very supportive and communicative throughout. Providing lots of helpful information beforehand, and stayed in touch during my stay, even over the smallest things. We came during the summer but would love to come back...
Luxurious Ski in-Ski Out Mnt. Creek/Hot tub/Tennis & Pickleball/Heated pool/Golf
Trails Head Cabin
Exterior

Trails Head Cabin

9.8 out of 10, Exceptional, (90)
"Great location that's super close to the trailhead, very convenient for those that want to hike in the area! Very easy check-in and reasonably priced. My partner and I had a wonderful time staying here."
The price is ￥16,073
￥29,785 total
includes taxes & fees
Sep 30 - Oct 1
Trails Head Cabin
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!
Interior

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

9.6 out of 10, Exceptional, (47)
"Love the hot tub, love the location Absolutely loved our stay! The place was clean, cozy, and exactly as described. Great location, easy check-in, and the host was super responsive."
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!
A luxurious stay.
Smart TV

A luxurious stay.

6.0 out of 10, (2)
"If you want to go to a diagusting neighborhood then this is your place. We felt so unsafe we didn’t even stay there. We got a hotel. It is that bad. As nice as the inside is, the outside and neighborhood will have you running. Music blasting stinks of weed homeless people all over. Do not book this place. The owner didn’t even refund us our cleaning fee. Trust me STAY AWAY."
The price is ￥18,751
￥42,257 total
includes taxes & fees
Oct 4 - Oct 5
A luxurious stay.
Lake Glenwood A-Frame Cabin stunning views, fire pit, game room, Pet Friendly
Terrace/patio

Lake Glenwood A-Frame Cabin stunning views, fire pit, game room, Pet Friendly

10.0 out of 10, Exceptional, (33)
"We had a nice and relaxing time in beautiful surroundings. Thank you for having this cabin. We really enjoyed the sunsets reflecting off the lake!"
The price is ￥26,206
￥56,737 total
includes taxes & fees
Oct 13 - Oct 14
Lake Glenwood A-Frame Cabin stunning views, fire pit, game room, Pet Friendly
Lakefront Haven • Private Beach • Dock • Fire Pit • Game Room • Boat Rental
Outdoor dining

Lakefront Haven • Private Beach • Dock • Fire Pit • Game Room • Boat Rental

10.0 out of 10, Exceptional, (2)
"Beautiful home, on a quiet street. Ample view from the living room, kitchen and deck/dock. We loved have a little private beach area for my daughter. The game room was such a fun bonus!! We will definitely be back !! "
The price is ￥42,417
￥83,938 total
includes taxes & fees
Sep 28 - Sep 29
Lakefront Haven • Private Beach • Dock • Fire Pit • Game Room • Boat Rental
Romantic spot above restaurant., ideal for the gourmet
Exterior

Romantic spot above restaurant., ideal for the gourmet

10.0 out of 10, Exceptional, (3)
"Hosts communicated well, the room was spacious and clean, and the restaurant downstairs is spectacular. "
The price is ￥22,323
￥28,621 total
includes taxes & fees
Oct 2 - Oct 3
Romantic spot above restaurant., ideal for the gourmet
Resort Getaway ! Mtn Creek Ski-In Ski-Out -Pool-Hot Tub-Sauna
Property grounds

Resort Getaway ! Mtn Creek Ski-In Ski-Out -Pool-Hot Tub-Sauna

10.0 out of 10, Exceptional, (66)
"We had a great stay."
The price is ￥21,197
￥43,680 total
includes taxes & fees
Sep 29 - Sep 30
Resort Getaway ! Mtn Creek Ski-In Ski-Out -Pool-Hot Tub-Sauna
Fenced Yard Private Lakes 7 Beaches Huge Fire Pit
Lake

Fenced Yard Private Lakes 7 Beaches Huge Fire Pit

9.8 out of 10, Exceptional, (103)
"Our 3rd time staying here. Fits our need perfectly. Great host nice home. Couldn't ask for anything more. Definitely will be back."
Fenced Yard Private Lakes 7 Beaches Huge Fire Pit
Our home is perfect for relaxing and having lots of fun, with near by activity’s
Terrace/patio

Our home is perfect for relaxing and having lots of fun, with near by activity’s

9.8 out of 10, Exceptional, (6)
"Really liked that each room had it's own temperature control"
Our home is perfect for relaxing and having lots of fun, with near by activity’s
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

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

10/10 Excellent
"Very nice. Out if the way with beautiful views. One problem: no elevator for older guests, and the website did not mention it. Perhaps put them on the first floor? It was not easy hauling suitcases up and down the long flight of stairs. Another guest also commented on it. If we had known, we could have requested a first floor room "
Shirley L 1-night trip
Posted 22 hours ago
Overlook Lodge at Bear Mountain

Find out more about Middletown

Find out more about Middletown

Search for holiday rentals in Middletown on Expedia! You can easily find your home rentals, villas, holiday apartments in Middletown using one of the methods below:

  • View our selection of featured holiday rentals in Middletown
  • Use the map to find apartments and other holiday homes in the Middletown neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Middletown while they last

Look no further and take a look at our great range of rental properties in Middletown!

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 12 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.