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

Middletown Holiday Rentals

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Our top choices for Middletown holiday rentals

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 NZ$738
includes taxes & fees
13 July - 14 July
Hello Small Stone

TRANQUIL MOUNTAIN SOLITUDE

TRANQUIL MOUNTAIN SOLITUDE
Pine Bush
10.0 out of 10, Exceptional, (7 reviews)
"Such a quaint & cozy little hideaway! Hosts could not be more hospitable. Thank you for a great stay!"
United States
Michelle H.
The price is NZ$419
includes taxes & fees
30 June - 1 July
TRANQUIL MOUNTAIN SOLITUDE

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 NZ$355
includes taxes & fees
30 June - 1 July
Trails Head Cabin

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 NZ$365
includes taxes & fees
30 June - 1 July
Cozy Loft Cabin high above Bashakill Wildlife Refuge

Cabin in the heart of the Hudson Valley, Cabin 4

Cabin in the heart of the Hudson Valley, Cabin 4
Newburgh
9.2 out of 10, Wonderful, (28 reviews)
"We LOVE this place and have stayed here twice."
United States
jennifer w.
The price is NZ$354
includes taxes & fees
30 June - 1 July
Cabin in the heart of the Hudson Valley, Cabin 4

House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
10.0 out of 10, Exceptional, (9 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is NZ$684
includes taxes & fees
30 June - 1 July
House on the Babbling Brook- Quiet 2BR + King Bed!

Luxe Loft 2 on Main St.Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!

Luxe Loft 2 on Main St.Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!
Warwick
10.0 out of 10, Exceptional, (48 reviews)
"The property is very cute and located in a great location. "
United States
Olivia R.
The price is NZ$441
includes taxes & fees
30 June - 1 July
Luxe Loft 2 on Main St.Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!

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, (38 reviews)
"Clean, welcoming, great location."
United States
Nicolae P.
The price is NZ$395
includes taxes & fees
5 July - 6 July
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (139 reviews)
"The space was comfortable and clean with a great view of the Hudson River valley. Perfect for 2 people on a weekend getaway. "
United States
Meredith C.
The price is NZ$580
includes taxes & fees
6 July - 7 July
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

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 NZ$534
includes taxes & fees
30 June - 1 July
Historic Cabin with Pool & Fire Pit

Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake
3.0 star property
Monroe
10.0 out of 10, Exceptional, (3 reviews)
"fantastic accommodations"
United States
David
The price is NZ$916
includes taxes & fees
2 July - 3 July
Hudson Valley Retreat w/ Pool Near Greenwood Lake

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 NZ$519
includes taxes & fees
13 July - 14 July
Grant - A Tranquil One Bedroom Steps from River

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 NZ$257
includes taxes & fees
30 June - 1 July
Trails Head Tiny House

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, (16 reviews)
"Perfect for the weekend event we were attending "
United States
Tara P.
The price is NZ$340
includes taxes & fees
12 July - 13 July
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Slope side cozy Studio

Slope side cozy Studio
Vernon Township
10.0 out of 10, Exceptional, (2 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.
The price is NZ$427
includes taxes & fees
1 July - 2 July
Slope side cozy Studio

Cabin in the Heart of the Hudson Valley, Cabin 1

Cabin in the Heart of the Hudson Valley, Cabin 1
Newburgh
10.0 out of 10, Exceptional, (35 reviews)
"Cute, clean and perfect for our needs"
United States
Richard H.
The price is NZ$496
includes taxes & fees
30 June - 1 July
Cabin in the Heart of the Hudson Valley, Cabin 1

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 NZ$311
includes taxes & fees
7 July - 8 July
Dream getaway apartment in the foot of Gunks Ridge

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, (85 reviews)
"great location and nice host"
United States
christopher s.
The price is NZ$421
includes taxes & fees
5 July - 6 July
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!

1BR Updated Condo at The Appalachian • Deck, Fireplace & Stunning Views #251

1BR Updated Condo at The Appalachian • Deck, Fireplace & Stunning Views #251
vernon
10.0 out of 10, Exceptional, (6 reviews)
"Everything was great! Easy check in, clean well appointed amenities in the room and location was great! Thank you "
United States
Heather K.
The price is NZ$562
includes taxes & fees
30 June - 1 July
1BR Updated Condo at The Appalachian • Deck, Fireplace & Stunning Views #251

Cozy country efficiency in the Hudson Valley

Cozy country efficiency in the Hudson Valley
Newburgh
9.8 out of 10, Exceptional, (69 reviews)
"Comfy cozy weekend retreat"
United States
Michael M.
The price is NZ$559
includes taxes & fees
1 July - 2 July
Cozy country efficiency in the Hudson Valley
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

Find out more about Middletown

Everything you need to know about Middletown holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Middletown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middletown holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Middletown holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middletown. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middletown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middletown holiday rentals we have selected for you start as low as NZ$269 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Middletown rentals

At Expedia, we put the best Middletown holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Middletown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middletown holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middletown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 Pool + Paddle Boats Sleeps 12: This holiday home rental outside of Middletown offers an outdoor pool, a balcony and air conditioning to help you feel perfectly comfortable in your new surroundings. You can relax into your holiday with a garden and a selection of games.

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. 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.