Photo by Vincent Ramundo

Holiday Rentals in Middletown

  • Plan, book, stay with confidence
  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Middletown

Cottage Suites

3.0 star property
8.0 out of 10, Very good, (3)
"The actual room was excellent, compfy bed. Shower door was hard to open. No handle on the outside. Loud cars going through the neighborhood and my room was up 3 flights of stairs. "
Cottage Suites

Lazy River Cottage on the Delaware River

10.0 out of 10, Exceptional, (130)
"We absolutely loved our stay at Lazy River Cottage! The cottage was clean, well-decorated, and full of light. The view of the river was stunning and such a delight to observe in the mornings. David was responsive to our needs. We highly recommend this property!"
Lazy River Cottage on the Delaware River

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (105)
"Super cozy apartment with a beautiful view. Very welcoming host and a great place for a short stay near Bear Mountain. "
The price is €245
includes taxes & fees
1 Dec - 2 Dec
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Located next to the Ski Resort, Bike Park and Water Park

10.0 out of 10, Exceptional, (153)
"It’s our second time staying in this condo. We love it and hope to use it again. "
Located next to the Ski Resort, Bike Park and Water Park

Trails Head Tiny House

9.0 out of 10, Wonderful, (10)
"Had a great stay at the Tiny House! Surprisingly clean and well appointed with all the basics. Perfect for an escape to the woods while still being able to quickly return to the real world. Proximity to the Neversink trail head is a major plus!"
The price is €123
includes taxes & fees
1 Dec - 2 Dec
Trails Head Tiny House

Trails Head Cabin

9.8 out of 10, Exceptional, (73)
"Great property right next to the State trails. Very dog friendly. "
The price is €204
includes taxes & fees
1 Dec - 2 Dec
Trails Head Cabin

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!

Beautiful Private Stone Home in the Hudson Valley

10.0 out of 10, Exceptional, (138)
"home and amenities enjoyed by all age groups. the city-slickers were thrilled by the deer, and visiting the chickens and roosters. the location is beautiful and rural. easy drive from nyc and capital district."
Beautiful Private Stone Home in the Hudson Valley

Lake Glenwood A-Frame Cabin w/stunning views, fire pit, game room & EV charger

10.0 out of 10, Exceptional, (21)
"The house is absolutely beautiful. My son named it the “Triangle House” Very clean. All supplies were available..towels, linens, etc. Plenty of activities to do in the area. We explored High Point State Park, went zip-lining at TreEscape, dinner in Warwick. Overall a great little getaway!"
Lake Glenwood A-Frame Cabin w/stunning views, fire pit, game room & EV charger

Fenced Yard Private Lakes 7 Beaches Huge Fire Pit

9.8 out of 10, Exceptional, (98)
"Great Highland Lakes Cottage! Clean & well stocked kitchen. Be careful going up or down Breakneck Rd. Thus time of year every view is beautiful! We did lots of small road trips taking in the sites and autumnal views!!"
Fenced Yard Private Lakes 7 Beaches Huge Fire Pit

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

Cozy Loft Cabin high above Bashakill Wildlife Refuge

9.2 out of 10, Wonderful, (15)
"Hikers’ Haven was a beautiful getaway. Vin was a great host and the cabin was cozy and well located"
The price is €155
includes taxes & fees
25 Nov - 26 Nov
Cozy Loft Cabin high above Bashakill Wildlife Refuge

Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!

9.8 out of 10, Exceptional, (43)
"Wonderful rental, clean, modern, and a beautiful location."
The price is €346
includes taxes & fees
2 Dec - 3 Dec
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!

Log Cabin in Catskill NYS

9.8 out of 10, Exceptional, (40)
"Our group of guys loved the cabin. It was spacious and convenient for 12 guys. The cabin was filled with amenities including thermostats in each room, towels, cookware, hot water, and cleaning/hygiene products. Peter and his family responded quickly to all of our messages and requests. This area is quiet and peaceful. The location is about 20-30 minutes from nearby restaurants, trails, and stores. "
Log Cabin in Catskill NYS

Lakefront Luxury on Greenwood Lake

10.0 out of 10, Exceptional, (125)
"What a great family trip. Great location. Great home.Views were outstanding. Owner was alway available and willing to help. Would stay here again when we return to the area. "
Lakefront Luxury on Greenwood Lake

Huge house with amazing kitchen, near great hiking; great for groups!

10.0 out of 10, Exceptional, (44)
"Northeastern's annual Alternative Weekend trips had an amazing stay over Veteran's Day weekend! The group volunteered with the local Woodstock Animal Sanctuary. Students and staff raved about the house!"
Huge house with amazing kitchen, near great hiking; great for groups!

Cozy Cabin with a Gorgeous View!

10.0 out of 10, Exceptional, (32)
"We thoroughly enjoyed our stay at the Cabin. It is a lovely space, with a large, open plan kitchen, dining and living area and two decently sized bedrooms. The main room has a wall of windows looking onto the river and the far bank. It is absolutely beautiful - and it's half a mile away from a large supermarket. It was the perfect place from which to visit High Point State Park and Stokes Forest. Our hosts were generous and gracious. We hope to visit again! I'm"
Cozy Cabin with a Gorgeous View!

Quaint village, walk to restaurants and shops.

9.8 out of 10, Exceptional, (9)
"Wonderfully quaint place within walking distance of downtown restaurants/pubs. Cant wait to come back"
Quaint village, walk to restaurants and shops.

Relax by the sea, Upper Delaware nearby

10.0 out of 10, Exceptional, (118)
"As we drove up to the house I got that warm feeling again. It was our second stay. Welcome home to me!!!! A cozy house for on the river. When you want to get away from the hustle and bustle play some games read a book by the fire place. This is the place for you. Like to fish or hunt or hike this is the place for you. All the amenities of home. "
Relax by the sea, Upper Delaware nearby

Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!

7.2 out of 10, Good, (11)
"Great space and very comfortable for a group "
The price is €826
includes taxes & fees
25 Nov - 26 Nov
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.
Don't see what you're looking for?
See all available properties in Middletown
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Middletown you may be interested in

La Quinta Inn & Suites by Wyndham Middletown

2.5 star property
9.2 out of 10, Wonderful, (566)
"It is a very friendly and nice hotel"
The price is €105
includes taxes & fees
17 Dec - 18 Dec
La Quinta Inn & Suites by Wyndham Middletown

Hampton Inn by Hilton Middletown

2.5 star property
8.6 out of 10, Excellent, (967)
"The gentleman at the counter was very nice. Hit it off with my father in law as they were both veterans. "
The price is €95
includes taxes & fees
20 Dec - 21 Dec
Hampton Inn by Hilton Middletown

Tru by Hilton Middletown

2.5 star property
8.4 out of 10, Very good, (804)
"Exceptional staff. Well maintained breakfast bar Convenient location"
The price is €115
includes taxes & fees
1 Dec - 2 Dec
Tru by Hilton 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.

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 free WiFi to help you feel content during your stay. Kitchen amenities include a stovetop, a coffee maker and kitchenware.

How many holiday rentals are there in Middletown?

With 14 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 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 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.