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Middletown Holiday Rentals

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Check prices for these dates

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

Holiday 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, (82)
"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 HK$1,462
HK$2,393 total
includes taxes & fees
30 Sept - 1 Oct
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 HK$1,113
HK$2,340 total
includes taxes & fees
3 Oct - 4 Oct
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
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 HK$1,540
HK$3,897 total
includes taxes & fees
1 Oct - 2 Oct
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
Mountain Creek Resort Condo - Golf, Hike, Legoland, Bike, NYC 1 Hour
Property grounds

Mountain Creek Resort Condo - Golf, Hike, Legoland, Bike, 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 HK$941
HK$2,140 total
includes taxes & fees
21 Oct - 22 Oct
Mountain Creek Resort Condo - Golf, Hike, Legoland, Bike, 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 HK$2,947
HK$4,264 total
includes taxes & fees
29 Sept - 30 Sept
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
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
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 HK$1,400
HK$2,501 total
includes taxes & fees
2 Oct - 3 Oct
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
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 HK$855
HK$1,932 total
includes taxes & fees
1 Oct - 2 Oct
Condo at Mtn Creek 1 Bdr 1 Bath sleep 4 Mtn view #234
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 HK$910
HK$1,635 total
includes taxes & fees
30 Sept - 1 Oct
Trails Head Cabin
Greenwood Lake Lakefront Luxury
Property grounds

Greenwood Lake Lakefront Luxury

10.0 out of 10, Exceptional, (142)
"We had the best time. The home was so clean and comfortable, and the views were beautiful. Cheryl is an amazing host and has stocked the home with everything needed to enjoy your stay. We hope to visit again!"
Greenwood Lake Lakefront Luxury
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 HK$980
HK$2,243 total
includes taxes & fees
1 Oct - 2 Oct
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!"
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 HK$1,834
HK$4,002 total
includes taxes & fees
5 Oct - 6 Oct
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 HK$1,166
HK$1,495 total
includes taxes & fees
30 Sept - 1 Oct
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 HK$1,101
HK$2,269 total
includes taxes & fees
29 Sept - 30 Sept
Resort Getaway ! Mtn Creek Ski-In Ski-Out -Pool-Hot Tub-Sauna
Cozy Loft Cabin high above Bashakill Wildlife Refuge
Terrace/patio

Cozy Loft Cabin high above Bashakill Wildlife Refuge

9.4 out of 10, Exceptional, (25)
"A fantastic little getaway after a wonderful day of hiking the Catskills! Vinny & Josh were perfect hosts and the property is fantastic! Will definitely be back! "
The price is HK$840
HK$1,381 total
includes taxes & fees
30 Sept - 1 Oct
Cozy Loft Cabin high above Bashakill Wildlife Refuge
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

Cottage Suites

Cottage Suites

6/10 Okay
"No staff but received my emails like I was supposed to with the two codes. Off street parking and a very well lit doorway and hallway. Room was clean and felt comfy to be there. I do have 2 negative remarks I feel need to be made, the room was clean however I did see a total of 3 roaches , two in the kitchen and one in bathroom. Didn’t panic on it as there is the Restaurant/store that may draw the critters but generally speaking where there’s one let alone 3 there is tons more not experiencing all of them was reassuring. The other remark I would like to mention is the unevenness of the floor. I sat at the desk and the chair had wheels and the next thing I know I’m rolling a wee bit done the room away from the desk. I did learn foot placement that would keep me from going across the room. So overall I’d rank it 3.5 stars almost four and if every I’m in the area again I would consider another stay there. "
JEANNE 3-night trip
Posted 2 days ago
Cottage Suites

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 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?

Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!: This holiday home rental outside of Middletown is located on a lake, and has an outdoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Middletown?

With 12 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 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 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.