House holiday rentals in Middletown

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Popular amenities for house rentals in Middletown

House rentals with a pool

Guest favourite
Home in Stormville
4.94 out of 5 average rating, 182 reviews

Private Hudson Valley Country Retreat

JackieRating, 5 stars2 weeks ago
This beautiful property has a special place in our hearts. We stayed in the A frame during COVID and we always wanted to come back. This time we stayed in the main house and it was phenomenal. Wish the weather was better for us to use the pool, but next time! It well worth the price. Only an hr from the city and it feels like a full vacation. Wonderful way to lose time time for a few days. We will be back!
Guest favourite
Home in Effort
4.98 out of 5 average rating, 147 reviews

Villa in the Sky - Best View of Pocono Mountains!

MichaelRating, 5 stars4 months ago
My girlfriend and I stayed in Jonathan’s home for our Valentine’s Day weekend. The house was beautiful and the views were amazing. Jonathan checked in on us to see if we had everything we needed and recommend local restaurants and places to visit he even gave us the time we should wake up to enjoy the sunrise which we did. All in all the trip was a 10/10 and we can’t wait to return!
Superhost
Home in New Paltz
4.86 out of 5 average rating, 159 reviews

Scenic River View Escape | New Paltz

TatiaRating, 5 stars3 weeks ago
I spent my birthday at this beautiful house and couldn’t have asked for a better experience. The place was spotless and full of natural light, with lovely views that made the stay even more special. The atmosphere was peaceful and clean, and the house had everything we needed for cooking and relaxing. I truly felt at home and appreciated all the thoughtful touches. Highly recommend for anyone looking for a cozy, well-equipped getaway!
Guest favourite
Home in Stamford
4.96 out of 5 average rating, 251 reviews

Midcentury Modern ZenHouse Sculptor Studio

EamonRating, 5 stars1 week ago
Truly one of a kind property. Relaxing, calm, extremely responsive and helpful host. If you are looking to get out of the city or just need some time away to think, look no further. 10/10.
Guest favourite
Home in East Stroudsburg
4.92 out of 5 average rating, 156 reviews

Sauna | Movie Theater | Hot Tub | Dogs OK |Firepit

NaudiaRating, 5 stars4 days ago
Place was absolutely beautiful! Plenty of room and Plenty of space for us to relax. Edwin was very responsive which made our trip go by so smoothly!
Superhost
Home in Gouldsboro
4.88 out of 5 average rating, 262 reviews

Lake Front Retreat in the Poconos * King Bed*

JoanneRating, 5 stars1 week ago
Great stay for my family of four and dog at this property on a beautiful part of the lake! Michael was super responsive at all times. House had everything we needed. Overall, a lovely home with a gorgeous view. Loved kayaking on the lake. At times no one else was there! Very peaceful!
Top guest favourite
Home in Lackawaxen Township
5 out of 5 average rating, 110 reviews

Wander Inn! Golf Sim, Hot Tub, Pools, Lake

KalebRating, 5 stars1 day ago
We rented this for my brothers bachelor party and it was the PERFECT spot. Super quiet area, tons of stuff to do in the house and in the community, not to mention Masthope mountain is a beautiful spot to be at! The house was awesome and all the amenities were great, the golf sim was down while we were there which was a bummer but everything else about it was amazing!
Guest favourite
Home in Narrowsburg
4.95 out of 5 average rating, 202 reviews

Modern House with Private Pool, Hot-Tub, Fireplace

AlexandraRating, 5 stars3 weeks ago
It was a beautiful stay and everything were just like the photos! We enjoyed our stayed!

Weekly house rentals

Guest favourite
Home in Newburgh
4.91 out of 5 average rating, 47 reviews

Welcome to Newburgh's Cozy Cove

BrianRating, 5 stars2 weeks ago
This was a cute cozy cottage, just right for 3 people. This house was perfect for our quick getaway. Close to all local restaurants and store, but far enough away from all the busy roads. Owners were very friendly and helpful. Very quick to respond when we needed something. Would recommend to others.
Top guest favourite
Home in Parksville
5 out of 5 average rating, 117 reviews

The Catskill Getaway • Near Bethel Woods & Hiking

AveshaRating, 5 stars2 weeks ago
First Stavros was a stellar host. Proactive in communication and always responsive. Very attentive, we had one small interruption with the wifi that he promptly addressed before we even noticed! The house property is absolutely stunning and gorgeous, peaceful, spacious, very beautiful. The house has everything well stocked. Kitchen had plenty. I can't find one thing to comment that isn't positive. We all enjoyed ourselves to the max. The most enjoyable was the three walls full of windows that made the thunderstorms so beautiful to watch in the living room. The little stream in the back so pleasant to sit silently. An incredible house and even more kind, generous and helpful host
Guest favourite
Home in Wurtsboro
4.97 out of 5 average rating, 62 reviews

Streamside Catskills Cabin

JennaRating, 5 stars1 month ago
We had such a relaxing weekend in the cabin. Highly recommend for a quick getaway from the hustle and bustle! Everything was as described and any questions were quickly answered. Overall a wonderful place to stay :)
Top guest favourite
Home in Montgomery
4.99 out of 5 average rating, 88 reviews

Modern Woodland Retreat, Hudson Valley & Catskills

MichaelRating, 5 stars4 days ago
We appreciated the cleanliness of the house, and it was a nice place to relax with friends and family both inside and outside around the fire. We would definitely stay again!
Guest favourite
Home in Pine Bush
4.95 out of 5 average rating, 41 reviews

Cabin96-Shawangunk Mountain View

JamesRating, 5 stars3 weeks ago
Incredible space and we had it to ourselves. I wondered if there had been another family in the unit next door, how quiet it might have been. I would recommend leaving a broom and dustpan so that the guests can sweep up after they depart and during their visit as crumbs and other detritus ends up on the floor and no good way to pick up after oneself. Views are spectacular and we had our binoculars to catch the birds and other wildlife that uses the lake as their home. Easy walk to the convenience store on the corner of Rt 52 and Weeds Road. Very sweet spot. We used our computer to watch a couple of shows, as it was not easy to navigate the smart TV, but we did not choose the spot to watch the tele, so no big deal for us. Overall, great place and I would stay again. Cheers!
Superhost
Home in Middletown
4.92 out of 5 average rating, 12 reviews

Lake trail retreat

MirandaRating, 5 stars2 months ago
Perfect quiet place for our weekend stay. Was in town for a truck show so the host made sure we had water hook up to wash our trucks when we got there. House was super nice and bigger than expected!
Guest favourite
Home in Kerhonkson
4.96 out of 5 average rating, 312 reviews

Architect's Hudson Valley Home in the Woods

BaptisteRating, 5 stars1 week ago
Olga's beautiful modern house in Upstate New York is a real gem nestled near a wild forest. The spacious house offers plenty of room to relax and unwind after a day exploring the area. The location offers a perfect blend of tranquility and adventure, with plenty of things to do in the surrounding area. Olga was a fantastic host – incredibly responsive and flexible, which made our stay even more enjoyable. The house itself is stunning, with modern amenities and stylish decor. We had a wonderful stay and highly recommend this Airbnb!
Guest favourite
Home in Middletown
4.95 out of 5 average rating, 78 reviews

Wawayanda Lodge - Port Jervis, Hudson River

SammuelRating, 5 stars1 week ago
We stayed for 5 nights and had a great experience. The place was clean, spacious, and had everything we needed — comfy beds, quality linens, a well-equipped kitchen, and even a washer and dryer. No issues at all during our stay. The host was excellent — super responsive and kind. We accidentally left something behind, and they reached out right away to confirm and offered to send it back. Really appreciated that level of care. Highly recommend! ⭐⭐⭐⭐⭐

Private house rentals

Superhost
Home in Mountain Dale
4.77 out of 5 average rating, 91 reviews

little cozy house in the village

StarRating, 5 stars2 weeks ago
Great price airbnb for the exclusive space you get. Easy seamless check in/check out instructions. Features a deck & grill. Massive tv in living room with Netflix. Tons of air conditioning/fan options. Host checked in to make sure my stay was good which i appreciated
Superhost
Home in Middletown
4.81 out of 5 average rating, 26 reviews

Country Modern Home w/5-Acre land Relax Retreat

JulieRating, 5 stars2 weeks ago
We stayed in this beautiful four-bedroom home, and it was perfect for our group, each couple had their own comfortable bedroom. The house was spotless, well-equipped, and had everything we needed. Communication with the host was excellent, all our questions were answered promptly and clearly. We would be happy to come back!
Superhost
Home in Middletown
4.9 out of 5 average rating, 96 reviews

Hudson Valley Log Cabin with Lake Access & View

Joseph MichaelRating, 5 stars6 months ago
This was a great quiet peaceful getaway for my family and I. We enjoyed the nature walks and the calmness of the environment. The place was clean and cozy. We enjoyed our stay very much.
Guest favourite
Home in Wurtsboro
4.95 out of 5 average rating, 42 reviews

The Alexandria - Wurtsboro, NY

ChristopherRating, 5 stars3 weeks ago
Second time staying here. Looking forward to a third stay next spring. Excellent communication and clean, comfortable house.
Top guest favourite
Home in Warwick
5 out of 5 average rating, 85 reviews

Beautiful Summer Warwick Escape! New Home!

Tanner and SophiaRating, 5 stars1 week ago
We had a great stay at Laura's place! They were great hosts that were very responsive and helpful and their barn themed home is great - it's new, very well decorated, and immaculately clean. The backyard was big - it rained most of our trip so we didn't use it much but was a great space our kid otherwise would have played a lot in. H It's right next to a deli/sandwich shop that we got breakfast sandwiches and YOU HAVE TO GO TO THE BELLVALE CREAMERY! It's one mile away and has the best view you'll ever have while eating ice cream. We've stayed at a lot of airbnb's and would 10/10 recommend this one if you're coming to the area.
Top guest favourite
Home in Barryville
5 out of 5 average rating, 17 reviews

Luxury Mountain Retreat with Panoramic Vista Views

PrashantRating, 5 stars2 weeks ago
I am in two minds about what to write in this review. On one hand, this property is truly mind blowing. It has been designed beautifully indoors and there is so much attention to detail. And then, the view…I’ve traveled a lot and the view blew my mind. On the other hand, I’m not sure I want too many other people to know about this gem..because I want to come back. And I am hoping this review doesn’t make that more difficult.
Guest favourite
Home in Woodridge
4.85 out of 5 average rating, 46 reviews

The First House

RachelRating, 5 stars3 weeks ago
Xiaoyun's place was serene, beautiful, and thoughtfully decorated. The place felt like a retreat in and of itself. They were also very responsive and proactive in providing us with check-in + checkout instructions, so the whole process was seamless. Everything worked as expected with the hot water, a/c, and a stocked kitchen. Thank you!
Guest favourite
Home in Bloomingburg
4.94 out of 5 average rating, 62 reviews

Quiet Homey Rustic Retreat

KarenRating, 5 stars2 weeks ago
A lovely spot! Clean, well laid out and cozy. We loved the porch and kids had a blast w the ping pong and air hockey. Nice big kitchen that we enjoyed cooking in! Comfy beds, great water pressure in the showers and AC was a plus w the humid day. We stayed here for a family trip to Lego land and it was a great location!

Quick stats about house rentals in Middletown

  • Total rentals

    10 properties

  • Nightly prices starting at

    ₹3,462 before taxes and fees

  • Total number of reviews

    140 reviews

  • Wifi availability

    10 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi and Pool

  • Local attractions

    Coney Island, Orange County Fair Speedway and ShopRite of Wallkill

Destinations to explore

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