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Compare 465 Vacation Homes in Middletown with updated reviews, rates, and availability.

Greenwoods of Warwick

9.8 out of 10, Exceptional, (8)
"Home was very clean. The host was very friendly & informative. The beds were very comfortable. We would highly recommend staying at this location. We will definitely stay here again. 👍 "
Greenwoods of Warwick

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

9.6 out of 10, Exceptional, (23)
"Great place for family ski vacation. Apt was clean, with amenities for cooking. Great fireplace. The ski areas are very kid friendly. The bunny slope was carved up into different trails for learning different skills. Didn’t need to drive to get things. Everything for a great stay was right on site."
The price is SAR 598
SAR 1,226 total
includes taxes & fees
3 Feb - 4 Feb
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

Riverfront modern house with beautiful views

2.0 star property
10.0 out of 10, Exceptional, (1)
"My husband and I had an amazing time. Absolutely beautiful home, great location, and overall amazing experience. "
The price is SAR 1,111
SAR 1,769 total
includes taxes & fees
28 Jan - 29 Jan
Riverfront modern house with beautiful views

Spacious Getaway! 7BR w Park & pool Scenic Views

Spacious Getaway! 7BR w Park & pool Scenic Views

Majestic RiverView Estate - Breathtaking Views

10.0 out of 10, Exceptional, (4)
"We booked a weekend away to celebrate family birthdays and were very happy to celebrate in such a special place. There was plenty of room for 11 of us (+ dog) and was a mix of modern touches and old world charm highlighting the legacy of the house. And the view of the Hudson was a highlight of our stay. Highly recommend!"
Majestic RiverView Estate - Breathtaking Views

Pet-Friendly ‘Pond View Loft' w/ Private Pool!

9.6 out of 10, Exceptional, (11)
"Overall, it seemed like the property manager was not ready for guests. The toilet instantly broke, the pool hadn’t been cleaned in probably weeks, and the apartment had stained sheets. It’s a nice place but really not worth the money."
Pet-Friendly ‘Pond View Loft' w/ Private Pool!

Hiking/Climbing Paradise- walking distance to Mohonk/Gunks/Minnewaska

9.8 out of 10, Exceptional, (92)
"This property was spectacular. Immaculately clean and every detail done well. From a fully stocked and ready to go kitchen, to comfortable beds, sheets and towels. I’ll be back to stay here again and the host Michelle couldn’t have done more. Having had a few disappointing stays in other properties of late, this was a welcome game changer!!!"
Hiking/Climbing Paradise- walking distance to Mohonk/Gunks/Minnewaska

Delightful Home w/ Fire Pit, Walk to Lake!

9.8 out of 10, Exceptional, (9)
"This was a cute house in a beautiful spot of NY. It was cozy and well taken care off. The neighborhood was quiet and beautiful also. We would come agian. "
Delightful Home w/ Fire Pit, Walk to Lake!

Catskills mountain gateway house.

9.8 out of 10, Exceptional, (14)
"House is spacious and clean. The little touches like the Christmas decorations, games, books etc. were greatly appreciated. Beautiful property. Would definitely return. "
Catskills mountain gateway house.

Bright Cornwall-On-Hudson Vacation Rental!

10.0 out of 10, Exceptional, (11)
"Excellent location in Cornwall-on-Hudson. Walking distance to coffee shop and restaurants. Happy to see Painter's Tavern has reopened. 2 Alices-a nice coffee shop to hang out. Home is bright and spacious with contemporary decor. Fully stocked. Two bathrooms a bonus for five of us. Planning to return next holiday season."
Bright Cornwall-On-Hudson Vacation Rental!

Updated Home w/ Patio Half Mile to West Point

10.0 out of 10, Exceptional, (23)
"Very well appointed home a short walk from the West Point gate that met all of our needs for a weekend of catching up, going for walks and attending a wedding. Property is close to Storm King Art Center which is a great way to spend a beautiful afternoon. We lost power for 17 hours (neighborhood transformer blew) and the owners could not have been more helpful. Would highly recommend this house. "
Updated Home w/ Patio Half Mile to West Point

Our Rockbound Highland Home - 2 Blocks from Thayer Gate - 1/2 Block to Main St.

10.0 out of 10, Exceptional, (37)
"Review of VRBO Home - Our Rockbound Highland Rating: ⭐⭐⭐⭐⭐ (5/5) - Exceeded Expectations I recently stayed at a VRBO home that completely surpassed my expectations! The home was not only beautiful but incredibly comfortable, offering all the amenities promised in the listing. It felt like a home away from home and matched the online photos perfectly, which made our stay even more enjoyable. The check-in process was seamless, and the communication with the property manager was top-notch. This...
Our Rockbound Highland Home - 2 Blocks from Thayer Gate - 1/2 Block to Main St.

Red Cabin Lake House with Amazing Views!

2.0 out of 10, (1)
"Fishing/Lake: There is absolutely no access to the lake, including the community beach. No swimming. No fishing. Such details must be in the property's details in caps. Fishing or swimming is not allowed. Water: Smelly brown water in the house. You can’t drink it or cook with it or even take a shower. It is disguising. No heads-up about the water issue. Kitchen: The smell of dirty dishes welcomed us. It looks like the previous renters left them there. Only 4 forks and 1 knife in the house....
Red Cabin Lake House with Amazing Views!

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

10.0 out of 10, Exceptional, (1)
"Alexis was a great host and she was super communicative and easy to reach. The house was clean and prefect size for my group of 6. Most things were stocked but I’d reach out to the host in advance so you can buy anything that isn’t ahead of time. One important thing to note is that the driveway can only fit 2 cars and there isn’t really any street parking. "
BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.

Very Private Large Home on 22 Acres with Outdoor Kitchen

Very Private Large Home on 22 Acres with Outdoor Kitchen

Charming 3-bedroom house with WiFi, AC in marvelous Hudson Valley.

Charming 3-bedroom house with WiFi, AC in marvelous Hudson Valley.

Vernon Cozy 2BD Pet-Friendly Mountain Creek

The price is SAR 525
SAR 1,397 total
includes taxes & fees
30 Jan - 31 Jan
Vernon Cozy 2BD Pet-Friendly Mountain Creek

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

2.0 star property
9.0 out of 10, Wonderful, (4)
"Just what we needed with lots of space very clean and comfortable"
Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons

Elegant and spacious home with sauna and heated pool

10.0 out of 10, Exceptional, (1)
"We had a great stay! Cozy vibes and beautiful home. Would love to go back. "
Elegant and spacious home with sauna and heated pool

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!
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 property types 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

Royal Garden Main Cabin

9.6 out of 10, Exceptional, (4)
"ABSOLUTELY BEAUTIFUL!!! Its was a treat staying here. Its out in the country. Its called a cabin but its more of a house. The bedrooms were perfect and the beds were comfy. The property had a pond, and a fire pit. We seen 3 deer as we were pulling into the driveway. ABSOLUTELY RECOMMEND THIS RENTAL!!"
Royal Garden Main Cabin

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (106)
"Great place and host!"
The price is SAR 630
SAR 915 total
includes taxes & fees
26 Jan - 27 Jan
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
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.