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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, (72)
"10 guys stayed here for a weekend and had an excellent time. house is huge and very clean. we were there late march but I’m sure especially in the summer it’s a great getaway with a pool and lake access. "
Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (109)
"We enjoyed our stay. The views are great and the space comfortable. It worked well for our visit with family living nearby and visiting Bear Mountain."
The price is CA $233
CA $384 total
includes taxes & fees
Apr 30 - May 1
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Cozy Cabin with Sauna & Firepit!

9.6 out of 10, Exceptional, (24)
"We stayed at this cozy cabin in Monroe for 4 days since we were looking for a somewhat close location to West Point to visit our cadet. This cabin had plenty of room for the three of us. The floor plan was open, which was nice. The beds are comfy, and there are several useful amenities of which to take note. These included fresh towels for the bathroom and sauna, shampoo/conditioner/body wash dispensers in the bathroom, plenty of board games to keep you occupied, and a functioning T.V. I have to...
Cozy Cabin with Sauna & Firepit!

Private Lakefront Home With Kayaks * Stunning Sunsets * Panoramic View

10.0 out of 10, Exceptional, (287)
"The property is beautiful. It was cold when we were there, so we weren't able to take advantage of the outdoor amenities. The owner was very kind and communicated at a high level. I would highly recommend this property."
The price is CA $539
CA $719 total
includes taxes & fees
Apr 29 - Apr 30
Private Lakefront Home With Kayaks * Stunning Sunsets * Panoramic View

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

9.6 out of 10, Exceptional, (39)
"A wonderful host with a beautiful & comfortable home. All the necessities, plus more! A must stay at. "
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!

Cabin in the heart of the Hudson Valley, Cabin 4

9.0 out of 10, Wonderful, (21)
"Exactly as described."
The price is CA $151
CA $244 total
includes taxes & fees
Apr 29 - Apr 30
Cabin in the heart of the Hudson Valley, Cabin 4

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

10.0 out of 10, Exceptional, (53)
"This property was so cute! It had everything you needed. Relaxing and comfortable, the river was a gorgeous backsplash to the property. Kelly was always responsive and super sweet! All in all an amazing experience and such a cute town. "
The price is CA $165
CA $323 total
includes taxes & fees
May 5 - May 6
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!

Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.

10.0 out of 10, Exceptional, (48)
"This is an adorable cottage. It is very clean and well appointed. The kids (and adults) really enjoyed the detached game room. The hot tub and fire pit made for very relaxing evenings. We really enjoyed our time here. "
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.

Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick

Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick

Lazy River Cottage on the Delaware River

10.0 out of 10, Exceptional, (141)
"Owner thought of everything! Besides stocking the fridge, the amenities were top notch effort and planning. We sat and played games and talked in front of the picturesque view. The fireplace and sound system was a huge hit and helped set the mood. "
Lazy River Cottage on the Delaware River

Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC

9.8 out of 10, Exceptional, (59)
"Great location"
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC

Trails Head Cabin

9.8 out of 10, Exceptional, (78)
"Great place to relax near the Delaware Water Gap. Quiet and peaceful. "
The price is CA $187
CA $323 total
includes taxes & fees
May 1 - May 2
Trails Head Cabin

Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons

2.0 star property
9.0 out of 10, Wonderful, (6)
"This property is great, our stay here was just amazing from start to finish. Communication with the host was great, we left some items there and the host was super accommodating. Would recommend this property very highly."
Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons

2 Lake Cabins | Pool+HotTub | Game Room | 23acs

10.0 out of 10, Exceptional, (1)
"Gorgeous property for a family reunion. Host was very accommodating and responsive. Lots of fun amenities and room for everyone to spread out. Great open space on the lake but still felt private and quiet. Wifi throughout entire property. Absolutely recommend and would definitely book again."
2 Lake Cabins | Pool+HotTub | Game Room | 23acs

Expansive Views; Miles of River & Mountains Walk to Train, Main St, DIA

10.0 out of 10, Exceptional, (2)
"We had a lovely time staying in this beautiful space. What the listing does not fully capture is how well curated the space is, full of intriguing bits of Art and gracious style. An easy walk to DIA and the park on the river, and a very short drive into town made this a wonderful space for a getaway weekend! "
Expansive Views; Miles of River & Mountains Walk to Train, Main St, DIA

Spacious Getaway! 7BR w Park & pool Scenic Views

8.0 out of 10, Very good, (1)
Spacious Getaway! 7BR w Park & pool Scenic Views

Charming Inn Steps away from Downtown Warwick only an Hour away from NYC

The price is CA $118
CA $219 total
includes taxes & fees
May 19 - May 20
Charming Inn Steps away from Downtown Warwick only an Hour away from NYC

Perfect for Groups/Families! 5 Cabins, Pool, GameRoom & 30+ Beds at The Highland

2.0 star property
10.0 out of 10, Exceptional, (1)
"We had the most incredible stay at Highland! This property is perfectly set up for groups or families traveling together. With five separate houses/cabins, each couple (and their kids) had their own private space to relax and recharge—super comfortable and cozy, yet very clean and well-kept. It made the whole experience feel seamless and stress-free.At the same time, the shared space was perfect for gathering. We had the best time cooking and eating meals together, playing games, and just...
Perfect for Groups/Families! 5 Cabins, Pool, GameRoom & 30+ Beds at The Highland

Waterfront Modern Home with Fast Wifi & Hot Tub

9.8 out of 10, Exceptional, (16)
"Everyone loved our stay. The hot tub was even better than expected with the unexpected freezing temp and snow in April. House was clean and lake views were awesome. Plenty of space for families to spread out. We really enjoyed coming back to the warm and inviting space after our time at Legoland."
The price is CA $263
CA $696 total
includes taxes & fees
Apr 28 - Apr 29
Waterfront Modern Home with Fast Wifi & Hot Tub

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

10.0 out of 10, Exceptional, (25)
"Loved the home, so beautiful.. Couldnt enjoy the outdoor area due to ice, but would definitely go back again when it is warm out to enjoy the outdoor space. Gorgeous views!!!"
Lake Glenwood A-Frame Cabin stunning views, fire pit, game room, Pet Friendly
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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Other types of properties in Middletown you may be interested in

La Quinta Inn & Suites by Wyndham Middletown-Goshen

3.0 star property
9.2 out of 10, Wonderful, (682)
"Everything was okay. The breakfast needs some improvement. "
The price is CA $176
CA $207 total
includes taxes & fees
May 1 - May 2
La Quinta Inn & Suites by Wyndham Middletown-Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 star property
8.6 out of 10, Excellent, (1002)
"N/a"
The price is CA $157
CA $185 total
includes taxes & fees
May 26 - May 27
Sleep Inn & Suites Middletown - Goshen

Courtyard by Marriott Middletown Goshen

3.0 star property
8.6 out of 10, Excellent, (872)
"Great customer service "
The price is CA $152
CA $180 total
includes taxes & fees
May 4 - May 5
Courtyard by Marriott Middletown Goshen
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.

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. 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.