Apartment holiday rentals in Middletown

4.97 out of 5 average rating, 617 reviews

Apartment in Beacon

Luxe Loft 4 on Main St- Views! Steam Shower! W/D

Welcome to Luxe Studio #4 right on Main Street in Beacon. This is your home base for exploring the beautiful Hudson Valley! Walk to Dia Museum, train, restaurants, shops, galleries, hiking-all at your doorstep! Relaxing, meticulously clean space designed for comfort and indulgence with everything you could need- unforgettable steam shower, full kitchen, washer & dryer. Queen bed with luxe hotel-quality linens. 50” Toshiba 4K Fire TV, hardwood flooring, spacious bathroom with window &toiletries

ValueFamilyHeating

4.99 out of 5 average rating, 111 reviews

A serene sitting area features a low wooden table surrounded by plush cushions. Earth-toned decor enhances the calming ambiance. Light wood flooring complements the minimalist design, while natural light brightens the space through a nearby window.

Apartment in Port Jervis

Chichito's Japanese Retreat

Inspired by our travels to Asia and our love for the zen aesthetic, we welcome you to our cozy 2nd floor apartment on a duplex. A great place to take some time to relax and recharge from the hustle and bustle of life. Nestled in 16 acres of nature. A 1.5 hr drive from New York City, on the intersection of New York, NJ and Pennsylvania and a five minute drive to our charming small town of Port Jervis. Every detail of this home was put together with love in hopes that you make of it your haven.

LocationFamilyAmenities

The living area features a yellow sofa against a light-colored wall, complemented by a round black coffee table. A wooden dining table is positioned near large windows, which are dressed with sheer curtains. Stylish bar stools decorate the space near the counter, enhancing the inviting atmosphere.

4.91 out of 5 average rating, 118 reviews

Scenic 1-bedroom rental in Newburgh

Tranquil top floor apartment in a historic Newburgh building steps from the Hudson. Tastefully presented by Hendley & Co - a local design boutique - this unit offers serene views and all amenities you need for a comfortable stay. High end furnishings throughout provide a relaxing stay or a peaceful work environment. Ferry to Beacon within walking distance. Fast Wi-Fi, Samsung washer/dryer, and a walk-in rainfall shower. Monthly stays welcome. Please note several flights of stairs required.

LocationValueSleep quality

Superhost

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

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

ValueLocationNearby

4.81 out of 5 average rating, 303 reviews

4.96 out of 5 average rating, 123 reviews

Apartment in Goshen

Carriage House Apartment Close to Legoland NY

Immerse yourself in history in our newly renovated Carriage House, originally a historic horse barn, ensconced with hand hewn, exposed beams. This unique accommodation boasts modern amenities such as central air conditioning, a cozy fireplace, private laundry, and a fully working kitchen. Situated just a 4-minute drive from the renowned Legoland and opposite the prestigious Goshen Historic Race Track, we are perfectly positioned for both convenience and entertainment. @parkwayhousegoshen

ValueFamilyView

4.96 out of 5 average rating, 427 reviews

Apartment in New Paltz

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

ValueFamilyTV

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.

4.85 out of 5 average rating, 372 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!

FamilyLocationKitchen

4.97 out of 5 average rating, 456 reviews

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

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.

ValueLocationSleep quality

4.9 out of 5 average rating, 488 reviews

Apartment in Wallkill

Dream getaway apartment in the foot of Gunks Ridge

Beautifully decorated space full of original art located in the foot of Shawangunk Ridge on the side of a large farm field and a forest. Get together with friends at the handmade farm dining table, feel hygge next to a wood-fired place, enjoy nature tranquility, and recharge. We provide ALL you need: clean towels, cooking essentials, complimentary high-end loose tea /coffee, friendly atmosphere, and good local advice. Apartment is a half basement part of a house but has full privacy.

FamilyValueCleanliness

4.97 out of 5 average rating, 184 reviews

A serene pool area features a deep blue unheated swimming pool with steps leading in. A gazebo, softly illuminated by string lights, is nestled among lush greenery in the background. The natural landscape creates a tranquil retreat.

Apartment in Chester

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 15 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.

FamilyValueWalkability

Superhost

An overhead view captures a spacious living area with large windows allowing abundant natural light. A modern gray couch is positioned beside a round wooden coffee table on a patterned rug. A television is mounted on a wooden cabinet, with a green plant adding a touch of nature.

4.9 out of 5 average rating, 145 reviews

Airy Artsy Loft

Kick back and relax in this very spacious artist’s loft. There is one enclosed bedroom, one open loft space that serves as a second bedroom, and one full bath. This apartment features smart TV & High speed Fios WiFi, an in-unit laundry, and designer furnishings. Can accommodate 2-4 guests with one King bed and one Queen sized bed. Both are hybrid memory foam mattresses with natural cotton bedding for ultimate comfort and tranquility. One flights of stairs is required.

FamilyLocationLong stay

4.98 out of 5 average rating, 120 reviews

Centrally Located in the Heart ❤ of Newburgh

Built in 2018, our spacious second-floor apartment offers plenty of room for your group to relax and feel at home. Centrally located in Newburgh’s mid-Broadway commercial district, you’ll be close to historic sites, popular restaurants, local shops, and the attractions along Broadway and Liberty Street. The apartment also provides convenient access to nearby Hudson Valley towns and West Point.

FamilyLocationLong stay

Popular amenities for Middletown apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

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.

4.92 out of 5 average rating, 526 reviews

Riverview Rowhouse, a vintage modern home

ValueLocationSleep quality

4.85 out of 5 average rating, 781 reviews

A spacious kitchen and dining area feature light wood cabinetry and modern stainless steel appliances. A wooden dining table is complemented by white chairs, and a window seat provides natural light. Decorative elements include a bowl of fruit at the center of the table.

Apartment in Beacon

Top Floor 2BR

ValueFamilyOutdoor spaces

4.97 out of 5 average rating, 440 reviews

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

Warwick Village Apt w Off St Parking 2 GIG WIFI

FamilyValueSleep quality

Apartment in Greenwood Lake

The living space features a modern open layout, with a comfortable seating area including two black sofas and a coffee table. A wall-mounted television is positioned across from the seating. A dining table for four and a fully equipped kitchen are visible in the background, complemented by natural light from the windows.

A Suite Downtown- Lake access, hiking, and more!

LocationFamilyTV

4.95 out of 5 average rating, 154 reviews

4.99 out of 5 average rating, 253 reviews

Apartment in Beacon

Private Apt 2 Blocks MainSt/Roundhouse/MT/Maribeau

FamilyLocationParking

4.98 out of 5 average rating, 122 reviews

A spacious living area features a light-colored sofa with decorative cushions. A wooden coffee table sits in front, accompanied by two stylish dining chairs at a small table. Natural light fills the room through large windows, enhancing the welcoming atmosphere.

Apartment in Cold Spring

Charming Village Base. Walk to Restaurants & Shops

FamilyLocationCheckout

4.98 out of 5 average rating, 130 reviews

Apartment in Stony Point

Gorgeous Suite w/ Private Entrance

LocationFamilyGetting around

4.96 out of 5 average rating, 24 reviews

Apartment in Montgomery

Cozy studio apartment with everything you need!

FamilyLocationPool

Private apartment rentals

4.89 out of 5 average rating, 94 reviews

Apartment in Port Jervis

Hudson Valley Escape | Walk to Downtown & Hiking

LocationValueComfort

A modern sofa is adorned with a mix of textured pillows in neutral and green hues. A soft throw blanket is draped casually across the back. Above, two abstract art pieces in muted tones complement the relaxed design of the space.

4.97 out of 5 average rating, 38 reviews

Lander pied-à-terre with outdoor movie & dog park!

LocationFamilyLayout

4.91 out of 5 average rating, 35 reviews

Apartment in Pine Bush

Explore and Relax On The Knoll

FamilyLocationLayout

4.89 out of 5 average rating, 18 reviews

River Views & Deck | River Suite on Washington

LocationKitchenAccuracy

4.94 out of 5 average rating, 18 reviews

The Firenze Suite

LocationParkingQuiet

The spacious living area features a cozy sectional sofa with decorative pillows, a desk with a lamp, and a comfortable Cal King bed. Bright natural light fills the room through multiple windows, complemented by neutral wall colors and contemporary artwork.

4.97 out of 5 average rating, 89 reviews

The Lakeside Suite- Hudson Valley Restful Retreat

FamilyValueCleanliness

An aerial view of a spacious living area is shown, featuring a large sectional sofa and a TV unit. Natural light streams through the skylights and large windows. A dining table with chairs is set nearby, with sliding doors leading to an outdoor deck.

4.96 out of 5 average rating, 93 reviews

Breathtaking view’s condo

LocationValueHospitality

4.85 out of 5 average rating, 47 reviews

A comfortable living area is showcased with a sectional leather sofa and a coffee table at the center. An accent wall features floral patterns, while a flat-screen TV is mounted on the opposite wall. A skylight allows natural light to enhance the space.

Apartment in Chester

“The Loaf” in Sugar Loaf NY

LocationFamilyAir conditioning

Apartment rentals with a hot tub

Two wooden Adirondack chairs are positioned on a grassy area, facing a serene landscape dotted with trees displaying autumn foliage. A small side table is set between the chairs, providing a space for refreshments. A shed is visible in the background among the greenery.

4.95 out of 5 average rating, 288 reviews

Countryside Couples Suite

FamilyLocationQuiet

4.97 out of 5 average rating, 329 reviews

An outdoor deck area features a private hot tub surrounded by wooden fencing and a shaded canopy. A hammock is positioned to one side for relaxation, and a red chair provides additional seating. Soft string lights are draped overhead, contributing to a serene atmosphere.

Apartment in Milford

The Still Life Studio- Centrally located Oasis

FamilyValueCondition

4.9 out of 5 average rating, 278 reviews

The log cabin is set amidst lush greenery and trees, featuring a sloped lawn that leads to the entrance. Solar panels adorn the roof, while diverse plant life and landscaping surround the home, creating a harmonious blend with nature.

Apartment in Philipstown

Foxglove Farm

LocationFamilyRiver

The exterior of The Appalachian Hotel showcases a charming combination of red and yellow hues. The building features a pitched roof and multiple balconies. In the foreground, a clear blue pool reflects the evening sky, while landscaped greenery surrounds the area.

4.96 out of 5 average rating, 130 reviews

Mtn. Creek Heated Pool HotTub Sauna Fire Place

ValueFamilyTV

4.97 out of 5 average rating, 650 reviews

Apartment in New Paltz

Relaxing Spa Retreat~Gorgeous View~Walk to Village

ValueFamilyHospitality

4.94 out of 5 average rating, 83 reviews

Swiss Spot

LocationValueOutdoor spaces

5.0 out of 5 average rating, 20 reviews

Large condo near Mountain Creek & Crystal Springs

LocationFamilyView

A cozy living area features a stone fireplace with a mounted flat-screen television above it. Natural light fills the space through several windows, complemented by sheer curtains. A comfortable sectional sofa and a plush armchair provide seating, creating an inviting atmosphere.