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Middletown Vacation Rentals

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Our top choices for Middletown vacation rentals

Cottage in Middletown

Hello Small Stone
9.6 out of 10, Exceptional, (5)
"The house was great. It was nice to sit and relax by the small pond in the back."
United States
John H.
$389 nightly
The price is $440
Dec 31 - Jan 1, 2026
Total with taxes and fees
Hello Small Stone
$411 nightly
The price is $486
Dec 31 - Jan 1, 2026
Total with taxes and fees
Nature Escape - studio in the forest
$165 nightly
The price is $195
Dec 24 - Dec 25
Total with taxes and fees
Charming bungalow in lovely Middletown NY
9.8 out of 10, Exceptional, (14)
"Great Unit."
United States
Rudy R.
$263 nightly
The price is $266
Jan 20 - Jan 21, 2026
Total with taxes and fees
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
9.6 out of 10, Exceptional, (24)
"Over all the property was clean and staff was very cooperative. Only problems were the beds were very hard which made it hard for us to get a good nights sleep. The larger room had bugs but the owner took care of it right away. We enjoyed our stay."
United States
Harriet
$164 nightly
The price is $166
Jan 8 - Jan 9, 2026
Total with taxes and fees
Dream getaway apartment in the foot of Gunks Ridge
9.4 out of 10, Exceptional, (8)
"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.
$137 nightly
The price is $155
Jan 5 - Jan 6, 2026
Total with taxes and fees
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
10.0 out of 10, Exceptional, (32)
"Great time and great place to stay "
United States
S S.
$218 nightly
The price is $251
Jan 4 - Jan 5, 2026
Total with taxes and fees
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
3.0 star property
$272 nightly
The price is $308
Dec 30 - Dec 31
Total with taxes and fees
Hike & Fish: Outdoor Retreat Near Trails
10.0 out of 10, Exceptional, (7)
"Great weekend getaway to reconnect with old friends!"
United States
Lisa D.
$218 nightly
The price is $222
Jan 8 - Jan 9, 2026
Total with taxes and fees
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
9.8 out of 10, Exceptional, (42)
"Adorable place to stay in an adorable town! "
United States
Mary L.
$202 nightly
The price is $233
Jan 6 - Jan 7, 2026
Total with taxes and fees
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
9.2 out of 10, Wonderful, (25)
"We LOVE this place and have stayed here twice."
United States
jennifer w.
$169 nightly
The price is $200
Dec 24 - Dec 25
Total with taxes and fees
Cabin in the heart of the Hudson Valley, Cabin 4
9.4 out of 10, Exceptional, (6)
"We stayed in this unit and absolutely loved it. We were just a short drive away from the all the orchards in Warwick, NY. The accommodations were perfectly located with quite a few things to do in the area. We will stay again. "
United States
Jonathan O.
$220 nightly
The price is $249
Jan 20 - Jan 21, 2026
Total with taxes and fees
Cozy 1-bedroom condo-Ski in/out/Waterpark/King Bed/WIFI/Parking
9.6 out of 10, Exceptional, (41)
"Stan is really nice and helpful. The apartment is really well designed, spacious and clean, very well equipped with a nice porch. Stan is really thoughtful. Recommended!"
United States
Zohar
$229 nightly
The price is $259
Dec 29 - Dec 30
Total with taxes and fees
Grant - A Tranquil One Bedroom Steps from River
10.0 out of 10, Exceptional, (42)
"This was the best place to stay. Host was so nice to us. If we are in the area again we would definitely stay here again. "
United States
Eileen H.
$216 nightly
The price is $244
Jan 4 - Jan 5, 2026
Total with taxes and fees
Luxe Loft on Main St.- Steam Shower, ZeroG King Bed, Designer Kitchen, Elevator!
10.0 out of 10, Exceptional, (14)
"Can’t emphasize how nice the surrounding area and property itself are. Very relaxing while still being close to several small towns with great restaurants. Communication was excellent, overall a great experience! "
United States
jose f.
$171 nightly
The price is $173
Jan 8 - Jan 9, 2026
Total with taxes and fees
Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks
9.0 out of 10, Wonderful, (13)
"Nice convenient location, near the river and town. "
United States
Steve W.
$168 nightly
The price is $187
Jan 8 - Jan 9, 2026
Total with taxes and fees
★Rare River Views & Access, Cabin by Eden Islands★
10.0 out of 10, Exceptional, (4)
"Lovely quaint stay!"
United States
Kelly G.
$380 nightly
The price is $382
Jan 20 - Jan 21, 2026
Total with taxes and fees
Couple's Serenity Cabin * Hot Tub *Lake
10.0 out of 10, Exceptional, (6)
"Great little cottage close to Bethel Woods."
United States
Erin
$247 nightly
The price is $278
Dec 25 - Dec 26
Total with taxes and fees
Cozy Cottage with Woodstock Scavenger Hunt
10.0 out of 10, Exceptional, (6)
"House was clean and parking was easy! Close to downtown Port Jervis, with some great restaurants. The owners were so kind, and were so helpful!"
United States
Jen C.
$280 nightly
The price is $331
Jan 15 - Jan 16, 2026
Total with taxes and fees
Treeview - Cozy 2 BR Apartment - Fast WiFi ~ 1 hr from NYC - 5 mins to downtown
9.0 out of 10, Wonderful, (11)
"We were visiting for our daughtets wedding and needed a place mearby that accommodates pets. Nothing to look at on the outside but the inside is very nice. Very comfortableorganized and a good selection of teas and some coffee."
United States
ADAM K.
$168 nightly
The price is $187
Jan 12 - Jan 13, 2026
Total with taxes and fees
★Scenic Views & River Access, Cozy River Home ★
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Middletown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middletown vacation 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 low season months. For more hustle and bustle, you may prefer to visit Middletown in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $218 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Middletown rentals

At Expedia, we put the best Middletown vacation 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 vacation.

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 vacation rental in Middletown?

Yes, we offer vacation rentals in Middletown close to Orange County Fairgrounds, or you can go with a more remote option if you'd like a relaxing place to 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 vacation home rentals that Middletown has to offer?

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

How many vacation rentals are there in Middletown?

With 13 Expedia vacation rentals, you're sure 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 vacation rental in Middletown like?

Vacation rentals are privately owned properties you can book for short or long periods in Middletown. Vacation rentals offer extras such as hot tubs, fire pits, and patios so you'll have all the conveniences of home. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for a family getaway.