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Middletown Vacation Rentals

Vacation Rentals in Middletown

Cottage Suites
Luxury Studio | Private kitchen | Full-size fridge, microwave, oven, stovetop
Cottage Suites
3.0 star property
9.0 out of 10, Wonderful, 2 reviews
"The actual room was excellent, compfy bed. Shower door was hard to open. No handle on the outside. Loud cars going through the neighborhood and my room was up 3 flights of stairs. "
The price is $132
$280 total
includes taxes & fees
Jun 9 - Jun 10
Cottage Suites
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Property grounds
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, 96 reviews
"Comfortable apartment with a phenomenal view! The space could use a deep clean and some decluttering, but that view!!! Did I mention that the view was A-mazing?!?"
The price is $204
$284 total
includes taxes & fees
Jun 10 - Jun 11
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Lazy River Cottage on the Delaware River
Fireplace, books, music library, stereo
Lazy River Cottage on the Delaware River
10.0 out of 10, Exceptional, 119 reviews
"The cottage was perfect! Everything about the cottage was just as it was described. The cottage was neat as a pin upon arrival, we got in at night and David had the light on and music playing for us. Would definitely recommend the Cottage to others as the perfect weekend retreat."
Lazy River Cottage on the Delaware River
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Trails Head Tiny House
Exterior
Trails Head Tiny House
10.0 out of 10, Exceptional, 5 reviews
"It was great"
The price is $79
$124 total
includes taxes & fees
Jun 9 - Jun 10
Trails Head Tiny House
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
Property grounds
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
9.6 out of 10, Exceptional, 35 reviews
"Three nights here as we toured the area. Check in was easy. We were able to access the VRBO app 30 minutes prior to our arrival. By the time we reached the driveway, Ruben had sent the access code.The road to the house is gravel and only wide enough for one car. We were glad we had arrived during the day.The house has an antique store vibe. Lots of books for a rainy day activity. FYI, the photos on the listing are a bit different from what we saw in the rooms. The dining table is larger with...
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
1 bedroom, desk, iron/ironing board, travel crib
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
9.8 out of 10, Exceptional, 35 reviews
"This is a cozy property in a very rural setting. The host is extremely responsive and very thorough. It is quiet and private. The furniture and bed are very comfortable. The wood burning stove is a pellet stove which provides enough heat to take the edge off. The hot tub could comfortably fit 4 people. The Village of Cold Spring is less than 10 minutes away, as is the Interstate 84 bridge across the Hudson. If you want to make your own food, bring it. There is no grocery store nearby."
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
Lakefront Luxury on Greenwood Lake
Property grounds
Lakefront Luxury on Greenwood Lake
10.0 out of 10, Exceptional, 116 reviews
"This is our second visited and we are still in love with the Lake House!"
Lakefront Luxury on Greenwood Lake
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
Property grounds
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
10.0 out of 10, Exceptional, 37 reviews
"This end of the cul-de-sac accommodation is attached to the owners home. With a beautiful view from the attached patio I was happy to leave my screen door open any time I was there. The bedding and bed were comfortable and clean. The kitchen was fairly well stocked with cooking tools, plates, cups, coffee maker, toaster oven, dishwasher, towels, a fridge (bigger than a mini) with a filtered water dispenser. I will remember to bring my own tea bags if I stay again. The small bathroom was perfect...
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!
Fridge, microwave, oven, stovetop
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!
10.0 out of 10, Exceptional, 34 reviews
"Thanks so much for a great stay. This is such a wonderful place for large groups! Nice hikes in the area too, which we took advantage of. Kitchen and bar area was especially good for cooking and eating for 30+ people!"
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!
Entire Lakehouse Cabin by Mountain Creek & Warwick
Private kitchen | Fridge, microwave, oven, stovetop
Entire Lakehouse Cabin by Mountain Creek & Warwick
10.0 out of 10, Exceptional, 99 reviews
"Everything was great"
Entire Lakehouse Cabin by Mountain Creek & Warwick
Historic former hotel with amazing kitchen, near great hiking; great for groups!
Property grounds
Historic former hotel with amazing kitchen, near great hiking; great for groups!
10.0 out of 10, Exceptional, 36 reviews
"I was looking for somewhere that had many rooms for single and couple adults to stay at for a long weekend birthday celebration. It was super difficult to find somewhere with rooms relatively the same size and separate/private, until I came upon this listing. That was the impetus, and the reality was even better than we could have imagined. We spent most of our time in the large kitchen/dining room: cooking, eating, laughing, conversing, and playing games. At nights we would all go into large...
Historic former hotel with amazing kitchen, near great hiking; great for groups!
Trails Head Cabin
Exterior
Trails Head Cabin
9.8 out of 10, Exceptional, 57 reviews
"This is a great property we have now stayed multiple times and the property owners make sure everything is perfect on arrival. Will be staying again!"
The price is $115
$194 total
includes taxes & fees
Jun 9 - Jun 10
Trails Head Cabin
Fenced Yard Private Lakes 7 Beaches Huge Fire Pit
Lake
Fenced Yard Private Lakes 7 Beaches Huge Fire Pit
9.8 out of 10, Exceptional, 91 reviews
"My family was down for the Spartan race weekend. The property is in a perfect location for proximity to the mountain, as well as Beaches and playgrounds for the kids. It comfortably fit four adults and two kids, and the fenced yard was great for the dog. Michael is a thoughtful and responsive owner, and we are looking forward to staying again next time we are down."
Fenced Yard Private Lakes 7 Beaches Huge Fire Pit
Cozy country efficiency in the Hudson Valley
Fridge, microwave, oven, stovetop
Cozy country efficiency in the Hudson Valley
9.8 out of 10, Exceptional, 41 reviews
"This was a perfect hideaway located 15 minutes from Beacon where the wedding was. It was reasonably priced and had so many cute accents. The host was on top of all the details and very nice in person. Would definitely recommend. The only thing I would say just for an fyi it’s better for a couple as it’s a full size bed. I went with my teen daughter and it was too small for both of us in the bed so we alternated the couch. Not a minus at all but more an fyi. Thanks so much for hosting us."
The price is $150
$216 total
includes taxes & fees
Jun 9 - Jun 10
Cozy country efficiency in the Hudson Valley
Serene Waterfront Log Cabin on 1 Wooded Acre with NEW REDUCED RATES FOR 2024!
Exterior
Serene Waterfront Log Cabin on 1 Wooded Acre with NEW REDUCED RATES FOR 2024!
9.8 out of 10, Exceptional, 157 reviews
"This cabin was just what we needed for a girl's weekend. The area is beautiful with more to do than meets the eye. The owners are pleasant and responsive."
Serene Waterfront Log Cabin on 1 Wooded Acre with NEW REDUCED RATES FOR 2024!
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
Smart TV, fireplace
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
9.4 out of 10, Exceptional, 13 reviews
"Nice place in a property that's past it's prime and could use a refresh."
The price is $159
$324 total
includes taxes & fees
Jun 10 - Jun 11
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
Cozy Cottage with a Pond 2
1 bedroom, free WiFi
Cozy Cottage with a Pond 2
6.8 out of 10, 9 reviews
"Safe quiet clean the only thing was the power went out (quick fix though) and the bed was so hard it hurt my back "
The price is $100
$130 total
includes taxes & fees
Jun 8 - Jun 9
Cozy Cottage with a Pond 2
Rustic Chic at Mountain Creek! Pool, Hot Tub, Sauna, Open ALL Year Round!
Outdoor pool, a heated pool
Rustic Chic at Mountain Creek! Pool, Hot Tub, Sauna, Open ALL Year Round!
10.0 out of 10, Exceptional, 38 reviews
"Great location: clean and comfy."
The price is $116
$231 total
includes taxes & fees
Jun 10 - Jun 11
Rustic Chic at Mountain Creek! Pool, Hot Tub, Sauna, Open ALL Year Round!
Spectacular Log Home Estate North Wing Apt
Property grounds
Spectacular Log Home Estate North Wing Apt
10.0 out of 10, Exceptional, 25 reviews
"All as represented. Had everything we needed for a lovely home away from home!"
Spectacular Log Home Estate North Wing Apt
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!
Fridge, microwave, oven, stovetop
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!
7.0 out of 10, Good, 6 reviews
"My family was in the area for an event. We had a very pleasant time and the house is spacious and perfect for a weekend getaway!"
The price is $510
$967 total
includes taxes & fees
Jun 8 - Jun 9
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!
Don't see what you're looking for?
See all available properties in Middletown
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.

Middletown Vacation Rental Travel Info

Number of vacation rentals
2
Popular accommodation
Middletown private vacation homes
Known landmarks
Paramount Theatre, Castle Fun Center and Highland Lakes State Park
International airports
Newark, NJ (EWR-Liberty Intl.) and Newburgh, NY (SWF-Stewart Intl.)

Other types of properties in Middletown you may be interested in

La Quinta Inn & Suites by Wyndham Middletown
Exterior
La Quinta Inn & Suites by Wyndham Middletown
2.5 star property
9.2 out of 10, Wonderful, 396 reviews
"Pool"
The price is $135
$160 total
includes taxes & fees
Jun 13 - Jun 14
La Quinta Inn & Suites by Wyndham Middletown
Tru by Hilton Middletown
Reception
Tru by Hilton Middletown
2.5 star property
8.2 out of 10, Very Good, 695 reviews
"Very good stay. Front desk was extremely nice."
The price is $126
$149 total
includes taxes & fees
Jun 16 - Jun 17
Tru by Hilton Middletown
Hampton Inn by Hilton Middletown
Exterior
Hampton Inn by Hilton Middletown
2.5 star property
8.6 out of 10, Excellent, 871 reviews
"I was there for a training, it was very nice to study."
The price is $135
$160 total
includes taxes & fees
Jul 8 - Jul 9
Hampton Inn by Hilton Middletown
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.

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 $79 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?

Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits: This vacation home rental outside of Middletown is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. It offers a garden, a selection of games, and a spa tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Middletown?

With 17 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 Lakes State Park 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 like LEGOLAND® New York and Woodbury Common Premium Outlets.

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.

Recent reviews of Middletown properties
Expedia verified reviews

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

5/5 Excellent
"What a beautiful stay room was bigger then expected so much to do in area loved our stay"
A verified traveler stayed at Overlook Lodge at Bear Mountain
Posted 2 days ago
Overlook Lodge at Bear Mountain