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Middletown Vacation Rentals

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Vacation Rentals in Middletown

Cottage Suites

3.0 star property
8.0 out of 10, Very good, (3)
"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. "
Cottage Suites

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (106)
"Super cozy apartment with a beautiful view. Very welcoming host and a great place for a short stay near Bear Mountain. "
The price is CA $241
CA $353 total
includes taxes & fees
Jan 7 - Jan 8, 2025
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Trails Head Tiny House

9.0 out of 10, Wonderful, (10)
"Had a great stay at the Tiny House! Surprisingly clean and well appointed with all the basics. Perfect for an escape to the woods while still being able to quickly return to the real world. Proximity to the Neversink trail head is a major plus!"
The price is CA $99
CA $163 total
includes taxes & fees
Dec 26 - Dec 27
Trails Head Tiny House

Lazy River Cottage on the Delaware River

10.0 out of 10, Exceptional, (132)
"Everything was amazing. We spent Thanksgiving here. We definitely come back!"
Lazy River Cottage on the Delaware River

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

9.6 out of 10, Exceptional, (38)
"The whole family had a great time! We would love to come back!"
5 Star Secluded Private Estate -Hot Tub, Pool+Ski >Southwoods Mountain Vacation!

Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!

7.2 out of 10, Good, (12)
"This home was just what our group of 16 needed to find rest, reconvene from the day’s activities, and prepare for all the next day’s activities. The town of Monroe was a great place to stay as it was centrally located for all the places we visited. "
The price is CA $1,085
CA $1,804 total
includes taxes & fees
Jan 17 - Jan 18, 2025
Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!

Fenced Yard Private Lakes 7 Beaches Huge Fire Pit

9.8 out of 10, Exceptional, (98)
"Great Highland Lakes Cottage! Clean & well stocked kitchen. Be careful going up or down Breakneck Rd. Thus time of year every view is beautiful! We did lots of small road trips taking in the sites and autumnal views!!"
Fenced Yard Private Lakes 7 Beaches Huge Fire Pit

Lakefront Luxury on Greenwood Lake

10.0 out of 10, Exceptional, (126)
"We needed a place to stay while visiting family in north jersey. This house was perfect - beautiful views, fairly close and clean. Now that we know it is here, we will stay again, God willing. "
Lakefront Luxury on Greenwood Lake

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

10.0 out of 10, Exceptional, (52)
"The view was so good I never turned the TV on once during my stay! I was in town for a wedding and having such a clean, comfy, convenient, and well-apportioned accommodation only added to the joy of the occasion. This is an add-on to the host's residence and it was a comfort to know they were nearby while I was able to enjoy my complete privacy. "
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC

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

9.6 out of 10, Exceptional, (21)
"Enjoyed the accommodation and all tge area had to offer. We did the Sky ride and Coaster So Great. Went to Warwick Apple Festival Awesomeness and Blue Arrow Farm for concert. Highly recommend "
The price is CA $229
CA $466 total
includes taxes & fees
Jan 7 - Jan 8, 2025
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

Trails Head Cabin

9.8 out of 10, Exceptional, (73)
"Great property right next to the State trails. Very dog friendly. "
The price is CA $179
CA $297 total
includes taxes & fees
Jan 7 - Jan 8, 2025
Trails Head Cabin

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

10.0 out of 10, Exceptional, (42)
"The perfect spot for a Beacon/Newburgh getaway! Great access to the towns, Storm King State Park, and Storm King Art Center! Lovely house, great game room (played so much ping pong and darts), and the hot tub was perfect."
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.

Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!

9.8 out of 10, Exceptional, (43)
"Wonderful rental, clean, modern, and a beautiful location."
The price is CA $229
CA $487 total
includes taxes & fees
Jan 12 - Jan 13, 2025
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!

Lake Glenwood A-Frame Cabin w/stunning views, fire pit, game room & EV charger

10.0 out of 10, Exceptional, (24)
"The house is beautiful and very clean. Fun game room. Excellent view of the lake. Many sitting areas to enjoy. They provide games and books as well. The owner Neil answered all our questions promptly. Local food leaves a lot to be desired. Definitely AVOID Sussex Sit n Chat diner and avoid Silvio’s Villa (food was severely overpriced and tasted like prison cafeteria food. ) "
Lake Glenwood A-Frame Cabin w/stunning views, fire pit, game room & EV charger

Log Cabin in Catskill NYS

9.8 out of 10, Exceptional, (40)
"Our group of guys loved the cabin. It was spacious and convenient for 12 guys. The cabin was filled with amenities including thermostats in each room, towels, cookware, hot water, and cleaning/hygiene products. Peter and his family responded quickly to all of our messages and requests. This area is quiet and peaceful. The location is about 20-30 minutes from nearby restaurants, trails, and stores. "
Log Cabin in Catskill NYS

Located next to the Ski Resort, Bike Park and Water Park

10.0 out of 10, Exceptional, (154)
"We loved staying here. It’s very clean. It’s right at the base of the slopes! Loved being able to cook breakfast there. The heated outdooor pool was a great unique experience in the winter! The checkin and out process was well explained and simple. It is small though. It felt tight for our family if 3. I couldn’t imagine a group larger than that. Absolutely recommend for your small group. "
Located next to the Ski Resort, Bike Park and Water Park

Huge house with amazing kitchen, near great hiking; great for groups!

10.0 out of 10, Exceptional, (44)
"Northeastern's annual Alternative Weekend trips had an amazing stay over Veteran's Day weekend! The group volunteered with the local Woodstock Animal Sanctuary. Students and staff raved about the house!"
Huge house with amazing kitchen, near great hiking; great for groups!

Cabin in the heart of the Hudson Valley, Cabin 4

8.8 out of 10, Excellent, (18)
"The description of the property was accurate; however, a few things surprised me that would have affected my decision to book or not. First, the house is located beside a busy road where traffic is moving all hours of the day and night at 35-55 mph. For some, this isn't a big deal. For others, it's not as quiet as described. Thankfully, I was delighted to see the room provided a noise machine. Secondly, there is no fan. Only the A/C and heater provided any air movement if you didn't want the...
The price is CA $156
CA $234 total
includes taxes & fees
Jan 7 - Jan 8, 2025
Cabin in the heart of the Hudson Valley, Cabin 4

Quaint village, walk to restaurants and shops.

9.8 out of 10, Exceptional, (9)
"Wonderfully quaint place within walking distance of downtown restaurants/pubs. Cant wait to come back"
Quaint village, walk to restaurants and shops.

Amazing Villa! Indoor Hotub 🌟🌟🌟🌟🌟, Heated Pool, Game Room -Sleeps 25+ Ski

9.6 out of 10, Exceptional, (20)
"Our stay was great! Host was great at communicating. Enough towels were supplied. Beds were very comfortable. Highly recommended!"
Amazing Villa! Indoor Hotub 🌟🌟🌟🌟🌟, Heated Pool, Game Room -Sleeps 25+ Ski
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

2.5 star property
9.2 out of 10, Wonderful, (593)
"It was a really a nice stay nothing to complain convenient supermarket across the street and not too far from Crystal Run Mall "
The price is CA $142
CA $167 total
includes taxes & fees
Dec 30 - Dec 31
La Quinta Inn & Suites by Wyndham Middletown

Hampton Inn by Hilton Middletown

2.5 star property
8.6 out of 10, Excellent, (995)
"Safe and organized clean"
The price is CA $121
CA $143 total
includes taxes & fees
Jan 10 - Jan 11, 2025
Hampton Inn by Hilton Middletown

Sleep Inn & Suites Middletown - Goshen

2.5 star property
8.6 out of 10, Excellent, (1000)
"Everything great, except for the three long hairs on shower wall."
The price is CA $125
CA $141 total
includes taxes & fees
Jan 7 - Jan 8, 2025
Sleep Inn & Suites 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?

Trails Head Tiny House: This vacation home rental outside of Middletown is situated on a river and has a barbecue grill and free WiFi to help you feel content during your stay. Kitchen amenities include a stovetop, kitchenware, and an electric kettle.

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 Highland Lakes State 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.