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 AU$576
includes taxes & fees
19 Apr - 20 Apr
Hello Small Stone

Trails Head Cabin

Trails Head Cabin
Rock Hill
9.8 out of 10, Exceptional, (108 reviews)
"Beautiful house, very clean I’m already checking availability for my next trip, family was happy and enjoy it "
United States
juan
The price is AU$291
includes taxes & fees
19 Apr - 20 Apr
Trails Head Cabin

Rustic Chic Stays - Walk to Mountain Creek Resort - Pool + Hot Tubs + Sauna!

Rustic Chic Stays - Walk to Mountain Creek Resort - Pool + Hot Tubs + Sauna!
Vernon Township
10.0 out of 10, Exceptional, (49 reviews)
"Stacey was phenomenal! An excellent host. The rental was absolutely spotless and one of the coziest beds I've ever slept in, in my life. "
United States
Ricardo S.
The price is AU$404
includes taxes & fees
7 May - 8 May
Rustic Chic Stays - Walk to Mountain Creek Resort - Pool + Hot Tubs + Sauna!

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, (44 reviews)
"The property is very cute and located in a great location. "
United States
Olivia R.
The price is AU$330
includes taxes & fees
30 Apr - 1 May
Luxe Loft 2 on Main St.Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!

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
9.2 out of 10, Wonderful, (14 reviews)
"I really enjoyed my stay. The room was very clean, the inn is well located in town and it is great having the restaurant below. Would stay here again! "
United States
Erin R.
The price is AU$209
includes taxes & fees
22 Apr - 23 Apr
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Tiny Home, King Bed & Hot Tub, Unit B

Tiny Home, King Bed & Hot Tub, Unit B
Ellenville
9.6 out of 10, Exceptional, (9 reviews)
"Everything was perfect. Don’t miss the owners restaurant either it’s great "
United States
Matthew
The price is AU$412
includes taxes & fees
21 Apr - 22 Apr
Tiny Home, King Bed & Hot Tub, Unit B

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, (134 reviews)
"Amazing place Thanks for the stay "
United States
Julien C.
The price is AU$378
includes taxes & fees
20 Apr - 21 Apr
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Two Full Baths in Newly Renovated ski golf Condo! New on Market!!

Two Full Baths in Newly Renovated ski golf Condo! New on Market!!
Vernon Township
10.0 out of 10, Exceptional, (34 reviews)
"Clean & organized, was a perfect location for our family trip."
United States
Rodney L.
The price is AU$454
includes taxes & fees
6 May - 7 May
Two Full Baths in Newly Renovated ski golf Condo! New on Market!!

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, (32 reviews)
"Great overnight spot, especially with a dog."
United States
Ed C.
The price is AU$391
includes taxes & fees
19 Apr - 20 Apr
Cabin in the Heart of the Hudson Valley, Cabin 1

Historic Cabin with Pool & Fire Pit

Historic Cabin with Pool & Fire Pit
Montgomery
10.0 out of 10, Exceptional, (3 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 AU$289
includes taxes & fees
19 Apr - 20 Apr
Historic Cabin with Pool & Fire Pit

Cozy 2BR condo w/ valley views

Cozy 2BR condo w/ valley views
Vernon Township
9.6 out of 10, Exceptional, (26 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 AU$355
includes taxes & fees
19 Apr - 20 Apr
Cozy 2BR condo w/ valley views

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 AU$391
includes taxes & fees
19 Apr - 20 Apr
Cabin in the heart of the Hudson Valley, Cabin 3

Hike & Fish: Outdoor Retreat Near Trails

Hike & Fish: Outdoor Retreat Near Trails
3.0 star property
Westbrookville
The price is AU$429
includes taxes & fees
19 Apr - 20 Apr
Hike & Fish: Outdoor Retreat Near Trails

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, (8 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is AU$555
includes taxes & fees
19 Apr - 20 Apr
House on the Babbling Brook- Quiet 2BR + King Bed!

Country House w/Hot Tub, Deck, Grill & Fire Pit

Country House w/Hot Tub, Deck, Grill & Fire Pit
Goshen
10.0 out of 10, Exceptional, (61 reviews)
"Very good host "
United States
Binyomin
The price is AU$717
includes taxes & fees
19 Apr - 20 Apr
Country House w/Hot Tub, Deck, Grill & Fire Pit

Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer

Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer
Beacon
10.0 out of 10, Exceptional, (54 reviews)
"We havld a good time. The room was comfortable and perfectly located!"
United States
Brandy C.
The price is AU$350
includes taxes & fees
30 Apr - 1 May
Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer

Top floor, Mountain facing 2Bd, 2Ba @ Mountain Creek

Top floor, Mountain facing 2Bd, 2Ba @ Mountain Creek
Vernon Township
10.0 out of 10, Exceptional, (4 reviews)
"Jennifer had all the details accounted for and the place was great."
United States
Paulo R.
The price is AU$651
includes taxes & fees
22 Apr - 23 Apr
Top floor, Mountain facing 2Bd, 2Ba @ Mountain Creek

Villa Verde B&B, Greenwood Lake NY, 1

Villa Verde B&B, Greenwood Lake NY, 1
Monroe
10.0 out of 10, Exceptional, (31 reviews)
"Great host. Home is very clean and well appointed. Would definitely stay here again."
United States
Thomas
The price is AU$446
includes taxes & fees
17 Apr - 18 Apr
Villa Verde B&B, Greenwood Lake NY, 1

Cozy Loft Cabin high above Bashakill Wildlife Refuge

Cozy Loft Cabin high above Bashakill Wildlife Refuge
Wurtsboro
9.4 out of 10, Exceptional, (27 reviews)
"Great weekend getaway, very communicative and easy to access"
United States
Marlon R.
The price is AU$250
includes taxes & fees
30 Apr - 1 May
Cozy Loft Cabin high above Bashakill Wildlife Refuge

Modern penthouse suite in a restored grain tower with private roof deck.

Modern penthouse suite in a restored grain tower with private roof deck.
Warwick
10.0 out of 10, Exceptional, (27 reviews)
"Wonderful stay!"
United States
Lisi M.
The price is AU$732
includes taxes & fees
26 Apr - 27 Apr
Modern penthouse suite in a restored grain tower with private roof deck.
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 favourite 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 depend 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 AU$378 per night. Entering your travel dates in the search wizard might find you 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?

Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9: This holiday home rental outside of Middletown is located on a lake, and has a patio, a BBQ and air conditioning to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Middletown?

With 11 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.