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Middletown Vacation Rentals

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Check prices for these dates

Tonight
Apr 6 - Apr 7
Tomorrow
Apr 7 - Apr 8
Next weekend
Apr 11 - Apr 13
In two weeks
Apr 18 - Apr 20

Vacation Rentals in Middletown

Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!
5 bedrooms, desk, iron/ironing board, free WiFi

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

9.0 out of 10, Wonderful, (71)
"The home was large enough to accommodate our family and it was extremely clean. We would stay there again. Communication was excellent."
Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!
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, (108)
"Awesome "
The price is ￥24,684
￥41,222 total
includes taxes & fees
Apr 7 - Apr 8
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
Outdoor dining

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

9.8 out of 10, Exceptional, (57)
"Clean and welcoming. Deck is a great attraction. Price point is what attracted me as we were visiting Beacon & couldn’t find a place that didn’t break the bank. Was a little surprised to discover that this is an apartment addition to an existing house; we could hear the family members inside, and I hope we weren’t too noisy for them. Overall cozy and a nice respite. Thank you."
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!

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!
Private Lakefront Home With Kayaks * Stunning Sunsets * Panoramic View
Outdoor dining

Private Lakefront Home With Kayaks * Stunning Sunsets * Panoramic View

10.0 out of 10, Exceptional, (284)
"I visited my college aged son over the weeend for a special event and wanted to stay somewhere with a little something special rather than a hotel. This property exceeded my expectations. Even with winter still lingering, the lake view was spectacular and was highlighted by the home's back wall of windows. Also, Don is a very responsive host and made sure the home had everything you could need - grill, grill tools, pots/pans, appliances, etc. I truly appreciated the hospitality. I hope to stay...
The price is ￥40,406
￥53,456 total
includes taxes & fees
Apr 11 - Apr 12
Private Lakefront Home With Kayaks * Stunning Sunsets * Panoramic View
Hiking & Climbing Paradise- walking distance to Mohonk,Gunks,Minnewaska
Property grounds

Hiking & Climbing Paradise- walking distance to Mohonk,Gunks,Minnewaska

9.8 out of 10, Exceptional, (93)
"We had a wonderful family long weekend at Michele’s beautiful home in the Hudson Valley. We were there to celebrate the birthdays of my husband, son, and grandson. The house was comfortable and well equipped to make meals. Michele the host couldn’t be more responsive. There are many great hikes and wineries close by. This was a 5 star expereince enjoyed by all."
Hiking & Climbing Paradise- walking distance to Mohonk,Gunks,Minnewaska
BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.
Miscellaneous

BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.

10.0 out of 10, Exceptional, (2)
"My family and I had a fantastic stay! The house was even more beautiful and spacious than we expected, making it the perfect home base for our weekend trip to Mount Peter. It was clean, cozy, and had everything we needed for a comfortable and relaxing stay. My parents live nearby in Warwick and this will definitely be my go-to VRBO recommendation for anyone visiting the area. We can’t wait to come back!"
BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.
Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick
Interior

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

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

Mountain View escape

10.0 out of 10, Exceptional, (50)
"We loved everything! Every detail was perfect. It’s beautifully decorated and super clean. Can’t wait to come back! The king bed is super comfy and the shower is amazing! "
Mountain View escape
Hillcrest Glasshouse - a minimalist modern retreat
Interior

Hillcrest Glasshouse - a minimalist modern retreat

10.0 out of 10, Exceptional, (10)
"I found this place after countless hours of research looking for the perfect getaway where I would eventually propose to my girlfriend. This place stunned us in every aspect. Their home was impeccably clean and intricately decorated, their amenities were awesome and easy to use thanks to their clear instructions (Highlights were: Sonos speakers, hot tub with bathrobes, Miele coffee machine, and the fire pit), and the view is unmatched. Seeing the reaction of my now fiancée as she walked around...
Hillcrest Glasshouse - a minimalist modern retreat
Expansive Views; Miles of River & Mountains Walk to Train, Main St, DIA
1 bedroom, desk, WiFi, bed sheets

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

10.0 out of 10, Exceptional, (1)
"Had a wonderful, relaxing stay here. Convenient location allowed us to walk everywhere we wanted to go!"
Expansive Views; Miles of River & Mountains Walk to Train, Main St, DIA
Trails Head Cabin
Exterior

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 ￥16,015
￥29,572 total
includes taxes & fees
Apr 7 - Apr 8
Trails Head Cabin
Cabin in the heart of the Hudson Valley, Cabin 4
Outdoor dining

Cabin in the heart of the Hudson Valley, Cabin 4

9.0 out of 10, Wonderful, (21)
"The cabin was great. We drove to Beacon (15min) and spent a day. We plan to return in the Spring/Summer. "
The price is ￥16,015
￥25,861 total
includes taxes & fees
Apr 7 - Apr 8
Cabin in the heart of the Hudson Valley, Cabin 4
Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons
Smart TV, fireplace

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
Large Catskills Private Property. Sunset Estate! ❤️ 5 Star, Hottub, Island, ski
Outdoor spa tub

Large Catskills Private Property. Sunset Estate! ❤️ 5 Star, Hottub, Island, ski

8.0 out of 10, Very Good, (20)
"Nothing negative to say really. Booked this house for 20 guests and it fit us all comfortably. Everything was clean and loved the way this house was layed out. Lots of room and many things to do even inside the house. Huge backyard. Host was very kind. Not many things like paper towel, toilet paper, garbage bags for 4 days with 20 guests as well as no washer and dryer as it’s listed."
Large Catskills Private Property. Sunset Estate! ❤️ 5 Star, Hottub, Island, ski
Catskills mountain gateway house.
Terrace/patio

Catskills mountain gateway house.

9.8 out of 10, Exceptional, (17)
"The house comfortably slept the six of us."
Catskills mountain gateway house.
Luxury 3 Br 2 Bath Condo With Steam Shower Ski Golf Relax
Fridge, microwave, stovetop, dishwasher

Luxury 3 Br 2 Bath Condo With Steam Shower Ski Golf Relax

8.8 out of 10, Excellent, (77)
"We enjoyed our stay at this condo. There was plenty of space for us to hang out and sleep. We used the kitchen a lot and for the most part it was well equipped. We could have used more things like larger bowls to mix things or for chips. The downstairs bathroom shower could also use a curtain so that the water doesn’t get everywhere. The condo was easy to find and check in. The owner reached out to make sure we were good which was nice. Overall our family was happy with the unit "
The price is ￥25,713
￥66,000 total
includes taxes & fees
Apr 7 - Apr 8
Luxury 3 Br 2 Bath Condo With Steam Shower Ski Golf Relax
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, (138)
"Went hoping to get away from it all... That was an understatement. The view was excellent, the cottage is just what the doctor ordered. Still well withing a simple drive to ANYTHING you need. The warmer months should bolster the feeling of tranquility. Great spot for sure"
Lazy River Cottage on the Delaware River
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
Fridge, microwave, oven, stovetop

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.
2 Lake Cabins | Pool+HotTub | Game Room | 23acs
Outdoor spa tub

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."
The price is ￥58,625
￥197,631 total
includes taxes & fees
Apr 17 - Apr 18
2 Lake Cabins | Pool+HotTub | Game Room | 23acs
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

Sleep Inn & Suites Middletown - Goshen
BBQ/picnic area

Sleep Inn & Suites Middletown - Goshen

2.5 star property
8.6 out of 10, Excellent, (1010)
"Easy on off access to 84"
The price is ￥17,565
￥20,747 total
includes taxes & fees
Apr 20 - Apr 21
Sleep Inn & Suites Middletown - Goshen
La Quinta Inn & Suites by Wyndham Middletown-Goshen
Exterior

La Quinta Inn & Suites by Wyndham Middletown-Goshen

3.0 star property
9.4 out of 10, Exceptional, (666)
"No issues "
The price is ￥16,860
￥19,916 total
includes taxes & fees
Apr 10 - Apr 11
La Quinta Inn & Suites by Wyndham Middletown-Goshen
Courtyard by Marriott Middletown Goshen
Fireplace

Courtyard by Marriott Middletown Goshen

3.0 star property
8.6 out of 10, Excellent, (853)
"Nice and clean. Kids liked pool."
The price is ￥14,238
￥16,817 total
includes taxes & fees
Apr 20 - Apr 21
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.