A large steel bridge spanning a river, surrounded by trees and buildings.

Middletown Holiday Rentals

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Check prices for these dates

In two weeks
24 Jul - 26 Jul
In two months
4 Sept - 6 Sept
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Middletown holiday rentals

Individually furnished, desk, free WiFi, bed sheets

Cottage Suites

Cottage Suites
3.0 star property
Middletown
6.6 out of 10, (7 reviews)
"It was a great place "
United States
Jose
The price is HK$831
HK$1,516 total
includes taxes & fees
12 Jul - 13 Jul
Cottage Suites
Interior

Hello Small Stone

Hello Small Stone
Middletown
9.6 out of 10, Exceptional, (5 reviews)
"The house was great. It was nice to sit and relax by the small pond in the back."
United States
John H.
The price is HK$1,269
HK$3,271 total
includes taxes & fees
9 Aug - 10 Aug
Hello Small Stone
Interior

Dream getaway apartment in the foot of Gunks Ridge

Dream getaway apartment in the foot of Gunks Ridge
Wallkill
9.6 out of 10, Exceptional, (29 reviews)
"Clean and quiet."
United States
Ted
The price is HK$670
HK$1,443 total
includes taxes & fees
13 Jul - 14 Jul
Dream getaway apartment in the foot of Gunks Ridge
Interior

Trails Head Tiny House

Trails Head Tiny House
Rock Hill
9.0 out of 10, Wonderful, (20 reviews)
"Host was very friendly and helpful. "
United States
Michael R.
The price is HK$698
HK$1,135 total
includes taxes & fees
22 Jul - 23 Jul
Trails Head Tiny House
Interior

Trails Head Cabin

Trails Head Cabin
Rock Hill
9.8 out of 10, Exceptional, (113 reviews)
"Was very pet friendly. "
United States
Kevin
The price is HK$1,058
HK$1,841 total
includes taxes & fees
16 Jul - 17 Jul
Trails Head Cabin
Property grounds

Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!

Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Wallkill
10.0 out of 10, Exceptional, (86 reviews)
"Clean place very responsive and helpful hosts!!"
United States
Larissa N.
The price is HK$907
HK$1,859 total
includes taxes & fees
12 Jul - 13 Jul
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Smart TV

Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (46 reviews)
"Great lil tranquil home. Had all the things you'd need with some bonus touches and Stan was very quick and easy to communicate with. "
United States
Jen G.
The price is HK$1,058
HK$2,323 total
includes taxes & fees
13 Jul - 14 Jul
Grant - A Tranquil One Bedroom Steps from River
Terrace/patio

Cabin in the heart of the Hudson Valley, Cabin 3

Cabin in the heart of the Hudson Valley, Cabin 3
Newburgh
9.8 out of 10, Exceptional, (14 reviews)
"We had a great stay, everything you need is provided. Would recommend to anyone."
United States
Bill W.
The price is HK$1,325
HK$2,213 total
includes taxes & fees
12 Jul - 13 Jul
Cabin in the heart of the Hudson Valley, Cabin 3
Exterior

Historic Cabin with Pool & Fire Pit

Historic Cabin with Pool & Fire Pit
Montgomery
10.0 out of 10, Exceptional, (4 reviews)
"This little cabin was exactly what we needed for our stay in NY. It looks just as described, was clean, and the location was perfect for all of the places we wanted to visit. Overall it was very cozy and relaxing and we can't wait to stay again! "
United States
Sarah A.
The price is HK$965
HK$1,845 total
includes taxes & fees
15 Jul - 16 Jul
Historic Cabin with Pool & Fire Pit
Interior

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Warwick
9.0 out of 10, Wonderful, (17 reviews)
"Great value and beautiful room and In ."
United States
Paul E.
The price is HK$952
HK$1,503 total
includes taxes & fees
12 Jul - 13 Jul
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Interior

Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks

Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks
Kerhonkson
10.0 out of 10, Exceptional, (15 reviews)
"It was great! "It's about a whale"."
United States
jwinegra W.
The price is HK$570
HK$1,255 total
includes taxes & fees
12 Jul - 13 Jul
Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks
Smart TV, books, stereo

Cozy little retreat far from the city

Cozy little retreat far from the city
Mountain Dale
9.6 out of 10, Exceptional, (7 reviews)
"Beautiful home VERY CLEAN neighborhood was quite was everything we were looking for would definitely stay here again and recommend to others "
United States
Chris G.
The price is HK$995
HK$1,612 total
includes taxes & fees
29 Jul - 30 Jul
Cozy little retreat far from the city
Interior

Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks

Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
Kerhonkson
10.0 out of 10, Exceptional, (39 reviews)
"Sweet place, very close to Minnewaska State Park which was great for us"
United States
Sueane
The price is HK$663
HK$1,349 total
includes taxes & fees
15 Jul - 16 Jul
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
Exterior

Tiny Home, King Bed & Hot Tub, Unit B

Tiny Home, King Bed & Hot Tub, Unit B
Ellenville
9.8 out of 10, Exceptional, (11 reviews)
"Quiet and lovely for a solo adventure with my dog. "
United States
Darcie B.
The price is HK$1,371
HK$2,431 total
includes taxes & fees
12 Jul - 13 Jul
Tiny Home, King Bed & Hot Tub, Unit B
1 bedroom, free WiFi, bed sheets

Cozy Loft Cabin high above Bashakill Wildlife Refuge

Cozy Loft Cabin high above Bashakill Wildlife Refuge
Wurtsboro
9.4 out of 10, Exceptional, (30 reviews)
"Great weekend getaway, very communicative and easy to access"
United States
Marlon R.
The price is HK$980
HK$1,745 total
includes taxes & fees
12 Jul - 13 Jul
Cozy Loft Cabin high above Bashakill Wildlife Refuge
Fireplace, books

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Kerhonkson
9.6 out of 10, Exceptional, (14 reviews)
"The cottage was welcoming, clean and cozy. We appreciated the special touches throughout. The indoor fireplace and sauna were a huge bonus "
United States
Anthony M.
The price is HK$1,032
HK$1,857 total
includes taxes & fees
16 Jul - 17 Jul
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Living area

Cozy 2BR condo w/ valley views

Cozy 2BR condo w/ valley views
Vernon Township
9.6 out of 10, Exceptional, (28 reviews)
"Very nice stay really clean and beautiful views thanks a lot enjoyed snowboarding at creek for the 2 days "
United States
Jacqueline
The price is HK$1,150
HK$2,491 total
includes taxes & fees
14 Jul - 15 Jul
Cozy 2BR condo w/ valley views
Beach

Beaver Lake Escape

Beaver Lake Escape
Rock Hill
9.6 out of 10, Exceptional, (37 reviews)
"The house was perfect! Hot tub was an awesome touch "
United States
jeana z.
The price is HK$1,164
HK$1,978 total
includes taxes & fees
12 Jul - 13 Jul
Beaver Lake Escape
1 bedroom, free WiFi, bed sheets, wheelchair access

Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen

Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
Warwick
10.0 out of 10, Exceptional, (44 reviews)
"Absolutely ideal comfort, cleanliness, amenities that are top notch for the kitchen and bathroom and luxury at the heart of Main Street in Warwick."
United States
Melissa V.
The price is HK$952
HK$2,115 total
includes taxes & fees
12 Jul - 13 Jul
Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
Exterior detail

Slope side cozy Studio

Slope side cozy Studio
Vernon Township
10.0 out of 10, Exceptional, (4 reviews)
"What a great stay my mother had in Joseph's Slope Side Cozy Studio. Beautiful accommodations that were clean and spacious with a lovely view. The host was incredibly attentive, with appropriate messaging from booking all the way to check-out. The price was reasonable, the resort is incredible, and we are actually thinking of spending some time there again. While we are not skiers, this is a lovely place to visit in the spring and summer for a fun get away. We would definitely book with...
United States
Anne Marie W.
Slope side cozy Studio
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

Holiday Inn Express & Suites Middletown - Goshen by IHG

Holiday Inn Express & Suites Middletown - Goshen by IHG

10/10 Excellent
"Great check in by friendly and helpful staff. Quick but great stay."
Andrea 1-night trip
Posted 3 hours ago
Holiday Inn Express & Suites Middletown - Goshen by IHG

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
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  • 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?

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi: This holiday home rental outside of Middletown is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

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.