House vacation rentals in Middletown

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Quick stats about house rentals in Middletown

  • Total vacation rentals

    Explore 10 vacation rentals in Middletown

  • Nightly prices starting at

    Middletown vacation rentals start at G$10,458 GYD per night before taxes and fees

  • Verified guest reviews

    Over 40 verified reviews to help you choose

  • Wi-Fi availability

    10 of Middletown vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Middletown rentals

  • 4.5 Average rating

    Middletown stays receive an average rating of 4.5 out of 5 from guests

Top-rated house rentals in Middletown

Guests agree: these houses are highly rated for location, cleanliness, and more.

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Top guest favorite
A contemporary house is displayed, featuring a sleek exterior of wood and metal. Expansive windows offer a view of the surrounding trees. A spacious deck extends from the structure, providing a seamless transition to the outdoor environment.
Home in Accord
4.99 out of 5 average rating, 104 reviews

Accord River House

Welcome to our house in the woods! 12 acres surrounded by trees and above a series of waterfalls along the Stony Kill, which runs all the way from Minnewaska State Park through our property and into downtown Accord. You can sit in a hammock outside, soak in our hot tub while listening to the river, or chill out inside with some tunes or the TV projector. Budding entomologists will enjoy the endless procession of bugs, ants, spiders, ticks, and other creepy-crawlies that is part of River House.

ValueLocationKitchen

Superhost
An indoor heated swimming pool is featured, surrounded by wooden paneling and illuminated by colorful LED lights. A hot tub is positioned beside the pool, with two lounge chairs placed nearby. Large windows offer views of the exterior while maintaining a cozy atmosphere.
Home in Newburgh
4.81 out of 5 average rating, 134 reviews

Entire Home, Private Indoor Pool

This unique specious and tranquil getaway private home includes an indoor heated swimming pool, hot tub, an outdoor space of 34 acres for you to enjoy nature, work out equipment, movie theater. Complete eat in kitchen, outdoor grill. washer and dryer, three bathrooms. Huge open space basement equipped with LED changing color light. Rooms have Wi-Fi LED light to connect music. The place sleeps 8 guests, in beds. Two additional twin mattresses.16 guests maximum. Hot tub take a while to heat up.

ValueLocationQuiet

Top guest favorite
A welcoming front porch is featured, with white railings and steps leading to a spacious entrance. A seating area is arranged on the porch, surrounded by trees with autumn foliage. The house displays a warm red exterior under a partly cloudy sky.
Home in Huguenot
4.97 out of 5 average rating, 272 reviews

Stargaze Lodge

The house is brand new. It is set back off the road. its just minutes from the D&H Canal & Neversink river , 15 min from Bashakill vineyards Oakland valley race track, also trains are available in either Port Jervis or Otisville & the same time to rt 17 or 84. 30 minutes to the Monticello casino or rt 97 Barryville also ski locations near both places , 35 minutes to Warwick and Chester legoland & Milford Pa ,Bethel woods, Milford PA. Legoland is only 35 minutes away, show many people coming

ValueFamilyHiking

Top guest favorite
Home in Greenwood Lake
5.0 out of 5 average rating, 224 reviews

Panoramic Lakeviews & Lush Garden | Beach Access

Our property boasts unparalleled views of Greenwood Lake and the mountains beyond. Our private garden features hundreds of plants and a seasonal waterfall cascading into a lily pond with fish and frogs. A shaded patio offers panoramic views and a gas grill. Guests get access to a private community beach. In winter, after skiing at nearby slopes, unwind in the claw foot tub or retreat to the cozy living room, with exposed wooden ceilings, fireplace, smart TV, record player and board games.

FamilyLocationTV

Guest favorite
A scenic pathway leads towards a charming log cabin, surrounded by a natural landscape of trees and grass. The cabin features a sloped roof and large windows, offering a welcoming appearance. A gravel area is visible in the background, enhancing the rustic setting.
Home in Bloomingburg
4.9 out of 5 average rating, 108 reviews

Quiet Homey Rustic Retreat

"Escape to the perfect blend of tranquility and excitement! This charming 3-bedroom log cabin, just 120 minutes from the hustle and bustle of New York City, offers the ideal retreat. Nestled 15 minutes from Resort Casino, 10 minutes from the vibrant Middletown shopping area, and a short drive to Woodbury Commons, Warwick, and Robberio Winery. Plus, family fun awaits just 20 minutes away at Lego Land. Your rustic haven awaits, where city convenience meets the serenity of a log cabin retreat!"

FamilyValueLaundry

Guest favorite
A welcoming porch features a ceiling light fixture, two comfortable black seating chairs, and vibrant flower arrangements with red and white blooms. The entrance door presents a decorative glass panel, contributing to the inviting atmosphere of the home.
Home in Port Jervis
4.93 out of 5 average rating, 281 reviews

Victorian At Orange Square Entire Home

Immediately Feel Welcome As You Walk On To The Pillared Front Porch With Its Cushioned Deck Furniture. Enter The Welcoming Foyer And Feel The Comfort Of Home. Sink Deep In The Stuffed Couches In Front Of The Remote Controlled Gas Fireplace. Enjoy Your Favorite Book Or The Smart TV Entertainment Center. If Inclined Cook A Meal In The Modern Kitchen And Dine In The Elegant Dining Room With A Wood Burning Fireplace. Fire pit in back yard that can be viewed from the 6 person 104 degree Jacuzzi.

FamilyValueLong stay

Guest favorite
A modern living area features a light grey sectional sofa accompanied by two matching chairs. A sleek wooden coffee table sits on a patterned rug. A flat-screen television is mounted on the wall, and natural light filters through the window, illuminating the space.
Home in Warwick
4.87 out of 5 average rating, 218 reviews

Renovated 2 Bedroom Apartment in Heart of Village

Our newly renovated apartment is the lower level of a 1920 Victorian in the heart of the Village of Warwick. It boasts 650 sq ft of space with 2 bedrooms, and a full kitchen and bath. You can walk to beautiful shops, parks, and restaurants, or drive (free off-street parking) only minutes to ski, golf, hike, or enjoy our local orchards and wineries. There's even a doughnut shop across the street! All this with a huge backyard with it's own babbling creek! Welcome to 69 South St.

LocationFamilyLong stay

Guest favorite
A charming log cabin is nestled in a lush green landscape, surrounded by trees and well-maintained lawns. The cabin features a welcoming porch and multiple windows, allowing natural light to fill the interior. A tranquil country setting is evident within the serene environment.
Home in Middletown
4.88 out of 5 average rating, 107 reviews

Hudson Valley Log Cabin with Lake Access & View

Come for a relaxing weekend or just a getaway from your busy life at our comfortable and cozy log cabin. Tucked away in a serene country setting and less than 2 hours away from New York City, it's an easy retreat to immerse yourself in enormous serenity, refreshing air and vibes. Wake up in the morning in the sound of birds chirping, and walk around the well-kept grounds, gardens, lake, trails and rolling hills of the connecting 50-acre property, it can simply be called "healing".

LocationValueCondition

Top guest favorite
A classic blue farmhouse with white trim has a symmetrical facade featuring double-hung windows and green shutters. The entrance is marked by a red door, flanked by two matching red containers. A spacious lawn surrounds the structure, accentuating its inviting presence.
Home in Chester
4.98 out of 5 average rating, 163 reviews

The Little Green Farmhouse

Built in the mid 1800s, this 2,400 square foot. 2 story farmhouse is a comfortable country getaway with space for the whole family. Nestled on 2.5 acres, the house is perfectly positioned between the villages of Warwick and Sugar Loaf. There are 4 bedrooms on the 2nd floor with the ability to sleep 8 people. There are also 2 full bathrooms, a dining room, living room, office space, fully equipped kitchen, and a bonus space with a table to play board games, cards or puzzles.

ValueFamilyHiking

Top guest favorite
A red house is surrounded by vibrant autumn foliage, highlighting orange and yellow leaves on trees. A gravel path leads to the home, with two chairs visible in the outdoor seating area. Natural landscaping complements the serene wooded setting.
Home in Middletown
4.98 out of 5 average rating, 218 reviews

Peace and quiet. Comfy, private house to relax in

Quiet property,almost 8 acres, of beautiful wooded property . Set back from the road. Many trails, wineries and breweries nearby. Legoland is 20 minutes away and many antique shops within 30 minutes or so. We live in the other house on the property, so we are accessible. You can take a stroll on the path by the stream or sit on the spacious 35 x 10 foot deck and enjoy the natural setting of the property. Fire pit is now available. Enjoy the night air and gaze at the stars.

FamilyValueHeating

Top guest favorite
The historic farmhouse displays a two-toned exterior with yellow and green siding. A welcoming porch is featured at the front entrance, with wooden steps leading up. The structure is surrounded by trees, and soft sunlight casts a warm glow on the façade.
Home in Goshen
4.97 out of 5 average rating, 109 reviews

Historic Hudson Valley Farm House

This lovely historic farm house in the heart of the Hudson Valley is the perfect location for your next get away. The relaxation begins as you turn onto our long private drive, watch for wild turkey and deer. This is the perfect spot if you are coming to the area for a wedding, to visit West Point or LEGOLAND, go hiking, skiing or just to sample the local craft breweries and wineries. For art and music lovers Storm King Art Center, Dia Beacon and Bethel Woods are nearby.

ValueFamilyGetting around

Superhost
An inviting backyard features an inground pool surrounded by a spacious patio area. Loungers are positioned alongside the pool, and a diving board extends over the water. A fenced perimeter provides privacy, with lush greenery adding a natural backdrop.
Home in Sussex
4.94 out of 5 average rating, 115 reviews

Mountain Creek retreat PH w/pool & hot tub

⸻ Welcome to The Spruce, a privately owned, modern farmhouse retreat less than 5 miles from Mountain Creek Ski Resort in Vernon, NJ. Relax in your private backyard oasis with a fenced-in pool, 6–7 person hot tub, two decks, BBQ grill, and outdoor fireplace. Explore nearby wineries, breweries, farms, and the charming town of Warwick, NY—just 15 minutes away. Whether you’re visiting for adventure or relaxation, The Spruce offers the perfect balance of comfort and luxury.

ValueFamilyLayout

Popular amenities for Middletown house rentals