Apartment vacation rentals in Middletown

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Top-rated apartment rentals in Middletown

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Top guest favorite
The living area features a cozy sofa in soft blue, complemented by a rug in neutral tones. Exposed wooden beams add character to the room, while a dining table and a chair are positioned nearby. Natural light fills the space through sliding doors leading outside.
Apartment in Goshen
4.97 out of 5 average rating, 228 reviews

Historic Horse Barn Sleeps 6/ 4 Minutes 2 Legoland

Completely renovated 2-bedroom apartment in a historic horse barn. A separate entrance for those looking for more privacy. Modern Full kitchen with stone countertops, Private In-Unit Washer & Dryer for your convenience. WiFi access and TV. Located directly across from Goshen Historic Track with a panoramic view of the world's oldest active harness racing track. Walk, bike, skate or scoot to quaint village restaurants, shopping, and attractions including the nearby Heritage Trail. 8 Units +

Guest favorite
A living area features a comfortable sectional sofa adorned with cushions and a low wooden coffee table. Natural light fills the space through two windows, while a floor lamp provides additional illumination. The interior is accented by warm, earthy tones and wooden flooring.
Apartment in Stone Ridge
4.92 out of 5 average rating, 548 reviews

Romantic Apartment in Historic Stone Ridge

Relax in this cozy apartment in our beautiful colonial house in the middle of historical Stone Ridge, NY. It offers perfect mixture of rustic and modern styles and is decorated with original art. Full kitchen is equipped with everything you need to prepare a great meal. It is perfect for all seasons and located within walking distance to restaurants, coffee shops, yoga studios, groceries. New Paltz, Woodstock, Minnewaska, Mohonk Preserves, Shawangunk Ridge are all within the short 20 min drive.

Guest favorite
A spacious studio apartment features a large bed with a striped coverlet and soft lighting from bedside lamps. A round dining table is positioned near a flat-screen TV, while two windows allow natural light to brighten the room, enhancing the cozy ambiance.
Apartment in Goshen
4.8 out of 5 average rating, 278 reviews

Great apartment- closest to Legoland

Large studio apartment in an historic luxury setting. Guests have a private entrance with parking to a first floor, fun studio. Our property boasts a private tennis/pickleball court for guest use and is situated directly on the Heritage Trail, which is perfect for biking and jogging. Our home borders several hundred acres of scenic rural property, yet we are conveniently located in the charming, historic Village of Goshen - within walking distance to restaurants and the Trotting Horse Museum

Guest favorite
The living area features a welcoming sofa set with soft, rounded chairs and a wooden coffee table. A rustic accent wall made of horizontal wooden planks adds character. Natural light fills the space, highlighting the art pieces and decor. A workspace is visible in the background.
Apartment in New Paltz
4.96 out of 5 average rating, 400 reviews

Modena Mad House

Our apartment is 6 miles from downtown New Paltz on a quiet and private setting only 1.5 hours from New York City, in the heart of Hudson Valley's Wine Country and apple/peach orchards. 1 bedroom apartment with separate kitchen living room and front porch. Fridge is stocked with eggs, bread, cheese, coffee, wine. We have a large HD screen TV and Roku, but no local cable. 7 miles from Mohonk Preserve and 10 miles from Gunks climbing area, and great Cross-country skiing. Self check-in

Superhost
A light-filled space features a well-equipped kitchen with modern appliances and a minimalist design. The wooden staircase, adorned with potted plants, leads to a cozy upper area. Natural light streams in through the window, illuminating the warm wooden flooring and vibrant area rug.
Apartment in Newburgh
4.84 out of 5 average rating, 335 reviews

Unwind in a Bespoke Downtown Studio W Laundry

A bright & creative studio apartment welcomes you! Totally renovated by us for our family, and now available to you. Pros: ♥Automated check in (no waiting!) ♥ Comfy queen sized murphy bed with a real mattress ♥ Open space hang out, work, play, etc ♥Walkable neighborhood ♥Custom design with unique features (hand made tile, Murphy bed, commissioned mural) Cons: ☆Second floor apartment (one flight of stairs) ☆Rooftop not available in late fall/winter ☆ Studio apartment Welcome home!

Top guest favorite
A serene pond is surrounded by lush green grass and natural landscaping. Smooth stones are placed along the edge of the water, reflecting the blue sky and distant hills. The area offers a peaceful atmosphere with hints of nature visible in the scenery.
Apartment in Middletown
4.93 out of 5 average rating, 169 reviews

Just Around The Corner

This roomy, modern and immaculate apartment is situated conveniently near town, but far enough away that you can enjoy the countryside. Enjoy the view of the pond and sounds of nature. A one bedroom that sleeps six with three queen beds in separate rooms divided by doors. (Please note the listing price is for 4 guests. Each additional guest is $25 per night). We are 6 min to Middletown, 18 min to Legoland, 21 min to Wallkill, 49 min to Warwick and just under one hour to Patterson, NY.

Top guest favorite
A rustic bench is positioned along a wooden fence, offering a vantage point of rolling hills adorned with autumn foliage. The scene captures a bright, open sky dotted with fluffy clouds, enhancing the natural beauty of the surrounding landscape.
Apartment in Marlboro Township
4.98 out of 5 average rating, 409 reviews

Cliff Top at Turtle Rock

Cliff Top retreat with a one hundred mile view of the Shawangunk's and the Catskill Mountains, surrounded by thousands of acres of ancient forest. Conveniently located in the Hudson Valley Wine and Orchard country. Twenty minutes from Beacon and New Paltz. Furnished with mid-century and 18th century period furniture and art work, yet with all the modern conveniences. Uber and Lift an easy five minutes away. The ancient forest contains many Stone Age rock shelters and calendar sites.

Top guest favorite
A modern kitchen features a round table surrounded by four wooden chairs. The walls are tiled in white, and a stainless steel stove is visible alongside a countertop with kitchen appliances. A vibrant painting of sunflowers adds a splash of color to the space.
Apartment in Warwick
4.98 out of 5 average rating, 409 reviews

Warwick Village Apt w Off St Parking

2 minutes to Warwick Village Farmers Market Our lovely apartment has earned 5 star reviews from over 300 guests. You'll love this private suite w private entrance Large kitchen, bedroom & stunning sun room loaded with plants Loved by gardeners, bicyclists, runners, artists, writers, diners, & shoppers. Visit Brew Pubs & Wineries, Woodbury Common, West Point, Catskills, Mt Peter, Mountain Creek, Heated bathroom floor & large shower Beautiful gas stove 300 MBPS Washer & dryer

Superhost
A bedroom features a spacious bed with neutral-toned bedding and decorative pillows. A small bedside table holds a clock, while a light fixture hangs above. The room is brightened by natural light streaming through a window with blinds, contrasting with the warm wooden floor and white walls.
Apartment in Newburgh
4.92 out of 5 average rating, 475 reviews

Riverview Rowhouse, a vintage modern home

Stylishly renovated 1890 Rowhouse in Newburgh's up-and-coming Washington Heights District. Enjoy your morning coffee with views of the Hudson River and Mountains. Just 75 minutes from NYC, this home is a short drive to the Newburgh Waterfront and Liberty Street's hip new shops and restaurants such as Ms. Fairfax, The Flour Shop, Liberty Street Bistro, Mama Roux, The Newburgh Brewery, and more. Close proximity to the Beacon Ferry and a short drive to the Beacon train station.

Guest favorite
A spacious main room is featured with high ceilings and a skylight. The kitchenette is visible alongside a dining table and chairs. A wooden coffee table sits in the living space, adorned with decorative items. Natural light flows through large windows framed by greenery.
Apartment in Chester
4.99 out of 5 average rating, 138 reviews

Private Country Getaway

This family-friendly apartment is an hour from NYC, with a private driveway and entrance. The location is ideal for a getaway in any season. In the Warwick Valley, the property is 10 min from Legoland, and 13 min from the NY Renaissance Festival, surrounded by vineyards, orchards, farms, breweries, state parks, skiing, and the Appalachian Trail. 5 minutes from historic Sugar Loaf and the Sugar Loaf Performing Arts Center. 15 min from Woodbury Commons Premium Outlets.

Top guest favorite
A welcoming studio space is furnished with a pink sofa, a wooden coffee table, and a dining area with a table and chairs. Light enters through a sliding glass door, revealing views of the wooded backyard. A small television is positioned near the seating area.
Apartment in Tillson
4.98 out of 5 average rating, 167 reviews

Woodland Neighborhood Retreat

Relax in a cozy studio in the peaceful woods. Tasteful high-quality touches will have you feeling comfortable right away! This is an ideal space for up to 2 adults and up to 2 children. We live upstairs & offer self-check-in. A rare find in the Hudson Valley, our neighborhood is mostly flat, with walkable, quiet roads, and excellent bird-watching. It's an easy bike ride to connect to the vast state-wide rail trail system & all that the Mohonk Preserve has to offer.

Top guest favorite
The exterior of a two-story home is presented, featuring a welcoming front porch with two chairs. A distinctive copper-colored roof complements the white siding and black shutters, while tall windows create a bright atmosphere. A stone pathway leads to the front entrance amidst landscaped grass.
Apartment in Chester
4.96 out of 5 average rating, 403 reviews

Luxury Apt/Sugar Loaf/10 Min To LEGOLAND

This lovely modern space was just built in 2015. The space is located in the quaint Hamlet of Sugar Loaf, New York Artisan Village, which is surrounded by the town of Warwick and Chester with Greenwood Lake just minutes away...and NYC is just 75 minutes. It's a second floor apartment with private front and back entrances. Rear deck overlooks spacious fenced in yard with pond view. Walking distance to 2 restaurants and deli. LEGOLAND just 8 miles!

Popular amenities for Middletown apartment rentals

Quick stats about apartment rentals in Middletown

  • Total rentals

    20 properties

  • Nightly prices starting at

    € 51 before taxes and fees

  • Total number of reviews

    290 reviews

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

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