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Middletown Vacation Rentals

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Vacation Rentals in Middletown

Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!

9.0 out of 10, Wonderful, (81)
"This beautiful getaway was just what we needed. Fresh air, nature, and a gorgeous home. Already planning our next trip back..."
Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!

Mtn Creek Resort Condo - Mountain Bike, Hike, Golf, Swim, Legoland, NYC 1 Hour

10.0 out of 10, Exceptional, (47)
"Excelente place to stay and the host was very attentive.Will definitely be back "
The price is CA $150
CA $369 total
includes taxes & fees
Sep 3 - Sep 4
Mtn Creek Resort Condo - Mountain Bike, Hike, Golf, Swim, Legoland, NYC 1 Hour

Resort Getaway ! Mtn Creek Ski-In Ski-Out -Pool-Hot Tub-Sauna

10.0 out of 10, Exceptional, (63)
"We had a great stay."
The price is CA $195
CA $395 total
includes taxes & fees
Sep 2 - Sep 3
Resort Getaway ! Mtn Creek Ski-In Ski-Out -Pool-Hot Tub-Sauna

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

10.0 out of 10, Exceptional, (305)
"The lake views at this house are absolutely worth the trip and the money. It's a beautiful spot. And the host, Don, is super responsive, thoughtful and accommodating. Highly recommend!"
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

Our home is perfect for relaxing and having lots of fun, with near by activity’s

9.8 out of 10, Exceptional, (6)
"Really liked that each room had it's own temperature control"
Our home is perfect for relaxing and having lots of fun, with near by activity’s

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (120)
"It has an incredible mountain and water view. "
The price is CA $258
CA $423 total
includes taxes & fees
Sep 3 - Sep 4
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

3-bedroom house in charming Forestburgh with WiFi, AC. Start your getaway now.

10.0 out of 10, Exceptional, (6)
"Lovely property in a serene and interesting setting. The hosts were so kind and communicative. We stayed for a night and enjoyed local sights and a concert in Bethel! "
The price is CA $248
CA $448 total
includes taxes & fees
Sep 1 - Sep 2
3-bedroom house in charming Forestburgh with WiFi, AC. Start your getaway now.

Ann Creek: Charming 2 BR fully renovated house at Greenwood Lake. Dog friendly.

10.0 out of 10, Exceptional, (6)
Ann Creek: Charming 2 BR fully renovated house at Greenwood Lake. Dog friendly.

Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

9.4 out of 10, Exceptional, (36)
"Nice and clean"
The price is CA $197
CA $422 total
includes taxes & fees
Sep 1 - Sep 2
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

Cabin in the heart of the Hudson Valley, Cabin 2

9.6 out of 10, Exceptional, (22)
"Perfect for a getaway weekend for my wife and I! Easy check-in, clean, and although it's off a busy road, we found it peaceful and quiet. Would definitely stay again!"
The price is CA $150
CA $242 total
includes taxes & fees
Sep 1 - Sep 2
Cabin in the heart of the Hudson Valley, Cabin 2

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

9.8 out of 10, Exceptional, (19)
"Clean, comfortable, beautiful views, cute little town. Super accommodating host. Couldn’t have asked for more. "
The price is CA $316
CA $757 total
includes taxes & fees
Sep 16 - Sep 17
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

2.0 star property
9.8 out of 10, Exceptional, (14)
"A group of girlfriends stayed for a 2 night visit. Everything was just as listed, the home was in the perfect location, well stocked, and beautiful inside. We would definitely return again. "
The price is CA $454
CA $690 total
includes taxes & fees
Sep 2 - Sep 3
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,

The price is CA $247
CA $831 total
includes taxes & fees
Sep 1 - Sep 2
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,

Cabin in the heart of the Hudson Valley, Cabin 4

9.2 out of 10, Wonderful, (25)
"Exactly as advertised "
The price is CA $150
CA $242 total
includes taxes & fees
Sep 3 - Sep 4
Cabin in the heart of the Hudson Valley, Cabin 4

5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!

9.6 out of 10, Exceptional, (47)
"Love the hot tub, love the location Absolutely loved our stay! The place was clean, cozy, and exactly as described. Great location, easy check-in, and the host was super responsive."
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!

Trails Head Tiny House

9.0 out of 10, Wonderful, (19)
"A lovely tiny house, great hosts "
The price is CA $110
CA $185 total
includes taxes & fees
Sep 8 - Sep 9
Trails Head Tiny House

Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

9.8 out of 10, Exceptional, (11)
"The place was wonderful! Even before check-in, Don was very communicative and made sure to ask about our preferences for one of the rooms.We had a fantastic stay — the home was very spacious, and the layout was perfect for a large family.The highlight for us was the beautiful lake view. We loved the outdoor seating area right by the water — perfect for relaxing with a coffee in the morning or unwinding in the evening. The kayaks were a great bonus and made for some fun time on the lake.We will...
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

Lake Glenwood A-Frame Cabin stunning views, fire pit, game room, Pet Friendly

10.0 out of 10, Exceptional, (31)
"We had a nice and relaxing time in beautiful surroundings. Thank you for having this cabin. We really enjoyed the sunsets reflecting off the lake!"
Lake Glenwood A-Frame Cabin stunning views, fire pit, game room, Pet Friendly

Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!

10.0 out of 10, Exceptional, (65)
"The yard and river are so beautiful. It’s a wonderful place to stay!"
The price is CA $129
CA $284 total
includes taxes & fees
Sep 1 - Sep 2
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!

Stylish & Peaceful Getaway on 3 Private Acres

2.0 star property
8.6 out of 10, Excellent, (7)
"The steps upstairs were worrisome, if you have any knee issues - this may not be the best option for a VRBO.This home was super clean, and beautiful however. Plenty of parking space for your guest.All supplies were provided."
The price is CA $396
CA $606 total
includes taxes & fees
Aug 31 - Sep 1
Stylish & Peaceful Getaway on 3 Private Acres
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

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, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middletown vacation rentals we have selected for you start as low as CA $110 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 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 6 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. 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.