Middletown Vacation Rentals

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Check prices for these dates

In two weeks
Feb 6 - Feb 8
In two months
Mar 20 - Mar 22
In three months
Apr 17 - Apr 19
In four months
May 15 - May 17

Our top choices for Middletown vacation rentals

Bed sheets

Nature Escape - studio in the forest

Nature Escape - studio in the forest
Middletown
$230 nightly
The price is $272
Jan 31 - Feb 1
Total with taxes and fees
Nature Escape - studio in the forest
Interior

Charming bungalow in lovely Middletown NY

Charming bungalow in lovely Middletown NY
Middletown
$166 nightly
The price is $196
Jan 24 - Jan 25
Total with taxes and fees
Charming bungalow in lovely Middletown NY
Fridge, oven, stovetop, coffee/tea maker

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.8 out of 10, Exceptional, (16 reviews)
"Great Unit."
United States
Rudy R.
$254 nightly
The price is $258
Jan 25 - Jan 26
Total with taxes and fees
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Terrace/patio

Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna

Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
Gardiner
10.0 out of 10, Exceptional, (7 reviews)
"Great weekend getaway to reconnect with old friends!"
United States
Lisa D.
$201 nightly
The price is $204
Jan 26 - Jan 27
Total with taxes and fees
Modern Zen Chalet at the Foot of Gunks w Mt. View and barrel outside sauna
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, (24 reviews)
"Serg’s place was comfortable and clean! It was a perfect location for me and my friends to stay while rock climbing in the Gunks. We did not feel cramped or unsafe and the complementary tea was a hit! One thing to note is that both of the beds were low to the ground (below knee level) so if someone has knee or back problems, it might be difficult to stand up out of bed. "
United States
Mary S.
$159 nightly
The price is $162
Jan 25 - Jan 26
Total with taxes and fees
Dream getaway apartment in the foot of Gunks Ridge
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, (14 reviews)
"Beautiful place tucked back in the woods. Very relaxing and incredibly clean. The free coffee was a nice touch too. Will 100% be returning to The Gunks because of this house. "
United States
Kyle T.
$165 nightly
The price is $167
Jan 26 - Jan 27
Total with taxes and fees
Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks
Dining

Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
Beacon
10.0 out of 10, Exceptional, (32 reviews)
"Great time and great place to stay "
United States
S S.
$216 nightly
The price is $249
Feb 10 - Feb 11
Total with taxes and fees
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
A heated pool

Cozy 1-bedroom condo-Ski in/out/Waterpark/King Bed/WIFI/Parking

Cozy 1-bedroom condo-Ski in/out/Waterpark/King Bed/WIFI/Parking
Vernon Township
9.2 out of 10, Wonderful, (7 reviews)
"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.
$256 nightly
The price is $289
Jan 26 - Jan 27
Total with taxes and fees
Cozy 1-bedroom condo-Ski in/out/Waterpark/King Bed/WIFI/Parking
Interior

Lovely 3BR Home with parking-Walk to WP Gate!

Lovely 3BR Home with parking-Walk to WP Gate!
Highland Falls
10.0 out of 10, Exceptional, (7 reviews)
"Lovely home, great location and space for my family to have privacy. Enjoyed the deck for morning coffee. Would book again. "
United States
Briana T.
$308 nightly
The price is $348
Feb 4 - Feb 5
Total with taxes and fees
Lovely 3BR Home with parking-Walk to WP Gate!
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
9.2 out of 10, Wonderful, (9 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.
$134 nightly
The price is $152
Feb 9 - Feb 10
Total with taxes and fees
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Interior

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

Luxe Loft on Main St.ZeroG King Bed, Designer Kitchen, Elevator!
Warwick
10.0 out of 10, Exceptional, (42 reviews)
"This loft is great! Well appointed with everything you need. "
United States
Jean L.
$219 nightly
The price is $248
Jan 26 - Jan 27
Total with taxes and fees
Luxe Loft on Main St.ZeroG King Bed, Designer Kitchen, Elevator!
Exterior detail

Treeview - Cozy 2 BR Apartment - Fast WiFi ~ 1 hr from NYC - 5 mins to downtown

Treeview - Cozy 2 BR Apartment - Fast WiFi ~ 1 hr from NYC - 5 mins to downtown
Port Jervis
10.0 out of 10, Exceptional, (6 reviews)
"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.
$266 nightly
The price is $314
Jan 26 - Jan 27
Total with taxes and fees
Treeview - Cozy 2 BR Apartment - Fast WiFi ~ 1 hr from NYC - 5 mins to downtown
Interior

Trails Head Tiny House

Trails Head Tiny House
Rock Hill
9.0 out of 10, Wonderful, (19 reviews)
"Host was very friendly and helpful. "
United States
Michael R.
$111 nightly
The price is $125
Jan 29 - Jan 30
Total with taxes and fees
Trails Head Tiny House
Apartment | 6 bedrooms

2 Lake Cabins Pool+hottub Game Room 23acs

2 Lake Cabins Pool+hottub Game Room 23acs
2.0 star property
Highland Lake
$814 nightly
The price is $920
Feb 1 - Feb 2
Total with taxes and fees
2 Lake Cabins Pool+hottub Game Room 23acs
Smart TV

Trails Head Cabin

Trails Head Cabin
Rock Hill
9.8 out of 10, Exceptional, (99 reviews)
"Really cozy stay I definitely have to come back during the summer months it was a beautiful experience !"
United States
Kimaya
$174 nightly
The price is $195
Jan 25 - Jan 26
Total with taxes and fees
Trails Head Cabin
Exterior

Cabin in the heart of the Hudson Valley, Cabin 2

Cabin in the heart of the Hudson Valley, Cabin 2
Newburgh
9.4 out of 10, Exceptional, (31 reviews)
"A very cute, convenient, and affordable stay with timely, friendly communication from the owner. Our dog loved it and we appreciated the ability to have a private place to stay."
United States
Sara B.
$169 nightly
The price is $200
Jan 25 - Jan 26
Total with taxes and fees
Cabin in the heart of the Hudson Valley, Cabin 2
Exterior detail

Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen

Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
Beacon
9.8 out of 10, Exceptional, (43 reviews)
"Adorable place to stay in an adorable town! "
United States
Mary L.
$203 nightly
The price is $234
Jan 25 - Jan 26
Total with taxes and fees
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
1 bedroom, desk, free WiFi, bed sheets

Couple's Serenity Cabin * Hot Tub *Lake

Couple's Serenity Cabin * Hot Tub *Lake
Milford
10.0 out of 10, Exceptional, (4 reviews)
"Lovely quaint stay!"
United States
Kelly G.
$359 nightly
The price is $362
Jan 25 - Jan 26
Total with taxes and fees
Couple's Serenity Cabin * Hot Tub *Lake
Fridge, microwave, oven, stovetop

Cozy Hudson Valley Retreat - 1950's Ranch Close to Everything

Cozy Hudson Valley Retreat - 1950's Ranch Close to Everything
Kerhonkson
9.8 out of 10, Exceptional, (24 reviews)
"Enjoyed our stay at this comfortable ranch home. It was clean and convenient to local attractions. Recommend this VRBO."
United States
Teresa S.
$256 nightly
The price is $287
Feb 14 - Feb 15
Total with taxes and fees
Cozy Hudson Valley Retreat - 1950's Ranch Close to Everything
1 bedroom, iron/ironing board, free WiFi, bed sheets

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, (31 reviews)
"Great overnight spot, especially with a dog."
United States
Ed C.
$236 nightly
The price is $279
Jan 26 - Jan 27
Total with taxes and fees
Cabin in the Heart of the Hudson Valley, Cabin 1
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

Quality Inn near Mountain Creek

Quality Inn near Mountain Creek

10/10 Excellent
"Clean rooms and updated!"
mario 1-night trip
Posted 3 days ago
Quality Inn near Mountain Creek

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 $196 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.

Explore a world of travel with Expedia

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 12 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.