House vacation rentals in Middletown

5 out of 5 average rating, 275 reviews

The entrance of the cottage is framed by lush greenery and vibrant foliage. A stone pathway leads to a welcoming front door, accentuated by an overhanging roof and outdoor lighting. The architectural details are complemented by the surrounding natural landscape.

Home in Kerhonkson

Cook House | Modern Cottage w/ Hot Tub & Fireplace

Featured in Vogue, Curbed, and Remodelista, Cook House is a fully renovated modern cottage in the Catskills with cozy minimalist vibes and kitchen gear designed to inspire your inner chef. Enjoy cooking while records spin across the Sonos. Eat al fresco on the porch, then head to the hot tub. Or binge your favorite show on the projection screen at the foot of the bed. Great for couples or individuals looking to relax and enjoy nature. Hosted by The Reset Club, a member of 1% for the Planet.

4.99 out of 5 average rating, 191 reviews

The A-frame cabin is surrounded by trees and set on a grassy area. A fire pit with seating is situated in front, with smoke rising gently in the evening light. The cabin's large windows reveal a welcoming interior, illuminated by natural light.

Home in Jeffersonville

BirchRidge A-Frame: Sauna/Firepit/Hiking/King Bed

Nestled in the Catskills Forest, less than 2 hrs from NYC you'll find Birch Ridge A-frame! This gorgeous 2 bedroom cabin is set on 6 private acres with hiking areas and a seasonal stream. Enjoy the wall of windows that create a magical stay with breathtaking views. This is the perfect place to relax, sit in the barrel sauna, hike through the private forest, roast marshmallows over the fire, and soak up the sounds of nature. A space that’s made for creating memories that will last a lifetime!

4.93 out of 5 average rating, 142 reviews

A cozy outdoor seating area is surrounded by trees and fallen leaves. Four red chairs are positioned around a wooden table, with a fire pit in the center. String lights are draped overhead, creating a warm ambiance in the natural setting.

Home in Livingston Manor

Parkston Schoolhouse

Relax and unwind in this historic converted one-room schoolhouse. Built in 1870, the Parkston Schoolhouse served all grade levels in the Livingston Manor area. The schoolhouse was retired and converted to a cozy cottage style home in the mid 20th century and has recently been renovated into a stylish tiny home getaway. The home is tucked into the hillside along the beautiful, winding Willowemoc Creek and is set amidst a lush Catskill landscape just a five minute drive from Livingston Manor.

4.87 out of 5 average rating, 873 reviews

A spacious living room features an oversized corner couch with patterned upholstery, inviting comfort. A rustic coffee table occupies the center of the room, complemented by a colorful area rug. Natural light enters through the glass door, enhancing the warm ambiance.

Home in Kerhonkson

Dream House in the Gunks

This cozy House is located on top of the Gunks a few miles away from Minnewaska State Park main entry. House is facing State forest and is a perfect getaway from hectic city life. The space has been carefully redesigned with a lot of details for guests to enjoy the stay. We are very serious about the cleaning/laundry process. Fast internet, complimentary high quality coffee and tea, natural body wash/shampoo. There are good restaurants, wineries, farms and great outdoor activities around.

4.87 out of 5 average rating, 166 reviews

A bright bedroom features two spacious beds covered with white linens and soft blankets. Large windows and skylights fill the room with natural light, showcasing views of greenery outside. Blue curtains frame the windows, and a wicker basket with towels is positioned on a side table.

Home in Monroe

Sunlit & Peaceful. Hot Tub. Monroe. 1hr fr NYC.

Welcome to our cozy retreat in Monroe, NY where relaxation awaits you. Our charming Home is bathed in natural sunlight, thanks to numerous windows and skylights, creating a warm and inviting ambiance. Nature lovers can explore the scenic Heritage Trail, perfect for leisurely walks or bike rides. If shopping is on your agenda, the Premium Outlets at Woodbury Commons are just a short drive away. For family fun, Legoland is a nearby attraction, promising excitement, and joy for all ages.

4.98 out of 5 average rating, 163 reviews

A charming lakeside home with a red metal roof sits on a wooden deck overlooking the water. Surrounding landscaping features a serene pond, rocks, and green shrubs, creating a peaceful atmosphere. The setting sun casts a warm glow on the tranquil scene.

Home in Greenwood Lake

Amazing Lakefront Haven! Beach, Views, Free Kayaks

Don't miss summer at the Lake! Escape to this beautiful 3BR home in Greenwood Lake with incredible lake and mountain views. Enjoy our neighborhood beach to swim, launch kayaks, or fish, just steps away! You'll love the huge deck, cozy living area, firepit, ping-pong, free kayaks, paddleboard & well-equipped kitchen. Ideal for families or friends, this tranquil hideaway promises memories that will last a lifetime! Nearby wineries, breweries, restaurants, hiking, & more! 1 hour from NYC

4.88 out of 5 average rating, 99 reviews

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

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".

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.

4.89 out of 5 average rating, 161 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.

4.98 out of 5 average rating, 188 reviews

A cozy living area features a green velvet sofa and a blue upholstered couch, arranged around a rustic wooden coffee table. Natural light fills the space through multiple windows, adorned with sheer white curtains. A small decorative rug adds warmth to the dark wood flooring.

Home in Middletown

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.

4.99 out of 5 average rating, 185 reviews

A spacious living area is highlighted by exposed wooden beams and a stone fireplace. A cozy seating arrangement includes a colorful blanket draped over a large sofa. Natural light pours in from windows, illuminating a charming work desk and decorative artwork on the wall.

Home in Greenwood Lake

Spectacular Lake Views from Every Room & Garden

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

The exterior of a charming farmhouse features a wraparound porch adorned with white railings, surrounded by lush greenery. The home displays a combination of wood siding and gabled rooflines under a partly cloudy sky, inviting relaxation in a serene outdoor setting.

4.99 out of 5 average rating, 162 reviews

Cozy guest suite bedroom plus living room

Skylands is a beautiful 20 acre property in the town of Warwick a couple of hundred yards away from an orchard great for apple picking weekends in the Fall. Lovely patios overlooking acre pond nice for relaxing with a glass of wine. Private Guest Suite comprised of sitting room with a fireplace Attached Bedroom has one double bed sleeps 2 people with ensuite bathroom. . Outside you have a front porch overlooking the pond exclusively for your use WARWICK PERMIT 33699

4.99 out of 5 average rating, 161 reviews

A spacious living area features large windows allowing ample natural light. A gray sectional couch is complemented by a mustard yellow chair and a round ottoman. Wooden flooring is contrasted by a blue area rug, adding warmth to the minimalist design.

Home in Newburgh

Balmville Mid-Century Gem & Work From Home Retreat

Gather with friends and family or enjoy a work from home getaway in this mid century gem, located in the lovely hamlet of Balmville. This section of the Hudson River Valley is known for its well-maintained historic homes, river views, and vibrant culture. Enjoy dinner and cocktails in the city of Newburgh just 1.5 miles away, or cross the bridge to Beacon (just 5 miles away) and enjoy all Main Street has to offer. Hike Mount Beacon, Breakneck Ridge, and more.

Vacation rentals for every style

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Popular amenities for Middletown house rentals

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Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.94 out of 5 average rating, 183 reviews

A serene view of a private lake is complemented by a well-maintained pool area. Lounge chairs and umbrellas are arranged around the pool, with lush greenery and trees framing the landscape. The clear water of the lake reflects the surrounding nature under a soft, cloudy sky.

Home in Stormville

Private Hudson Valley Country Retreat

4.86 out of 5 average rating, 162 reviews

An open living space is visible, featuring wooden beams that create a warm atmosphere. The dining area is filled with natural light, showcasing a wooden table surrounded by chairs, with modern light fixtures above. A staircase leads to the upper floor, enhancing the spacious design.

Home in New Paltz

Scenic River View Escape | New Paltz

4.96 out of 5 average rating, 252 reviews

A spacious outdoor pool is surrounded by a stone patio, nestled within a serene environment of tall trees. The pool features a diving board and is complemented by nearby planters. A main house can be seen in the background, enhancing the tranquil setting.

Home in Stamford

Midcentury Modern ZenHouse Sculptor Studio

5 out of 5 average rating, 165 reviews

A serene outdoor space features a heated saltwater pool surrounded by well-maintained grass. Lounge chairs are positioned along the pool's edge under the shade of a large tree, creating a peaceful area for relaxation. The property is bordered by a wooden fence and offers expansive views of the surrounding landscape.

Home in Pound Ridge

Peaceful Light-Filled Guesthouse 1 Hour From NYC

Home in Lackawaxen Township

5 out of 5 average rating, 111 reviews

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

4.95 out of 5 average rating, 204 reviews

A welcoming front patio is shown with two chairs positioned near the house. Surrounding lush green grass extends to the horizon, featuring a backdrop of gentle hills and a few distant buildings, including a red barn, under a clear blue sky.

Home in Narrowsburg

Modern House with Private Pool, Hot-Tub, Fireplace

4.95 out of 5 average rating, 277 reviews

An inviting in-ground saline pool is surrounded by lush greenery and trees. Sun loungers are placed nearby on a spacious patio, providing a serene outdoor space for relaxation. The pool area is framed by a well-maintained lawn and natural landscaping.

Home in Cottekill

Peace & Privacy - High Falls (hot tub & salt pool)

4.96 out of 5 average rating, 122 reviews

Home in Monroe

Lakefront/Legoland/HotTub/Heated Pool 1 hr to NYC!

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Weekly house rentals

4.92 out of 5 average rating, 48 reviews

A well-lit bedroom features a spacious white bed, complemented by light green curtains that frame a large window. A simple ceiling fan is installed for ventilation. The adjacent hallway leads to a cozy living area, showcasing a neutral color palette and decorative elements.

Home in Newburgh

Welcome to Newburgh's Cozy Cove

4.83 out of 5 average rating, 29 reviews

The exterior of a custom-designed home is presented, surrounded by lush green lawns and tall trees. A neatly paved driveway leads to the entrance, which is softly illuminated by path lights. The welcoming facade features multiple windows, allowing natural light to fill the interior.

Home in Middletown

Country Modern Home w/5-Acre land Relax Retreat

4.97 out of 5 average rating, 65 reviews

A charming cabin surrounded by lush greenery showcases a dark wooden exterior. Large windows allow natural light to fill the interior, while vibrant planters adorned with greenery line the entrance. A well-maintained yard features a stone pathway leading to the front door.

Home in Wurtsboro

Streamside Catskills Cabin

4.93 out of 5 average rating, 14 reviews

A covered porch features a small round table set for two, with a cup on one side. A stack of firewood is neatly stored nearby, and large windows provide views of the surrounding greenery.

Home in Godeffroy

Family friendly River Retreat Wi Fi~ Fireplace

5 out of 5 average rating, 17 reviews

A spacious living area is highlighted by a modern sectional sofa in muted tones. Large windows frame serene outdoor views, complemented by a stone fireplace. Sleek wooden beams span the ceiling, while light-colored walls enhance the airiness of the room.

Home in Barryville

Luxury Mountain Retreat with Panoramic Vista Views

The spacious living area features a modern sofa arranged around a unique coffee table on a patterned rug, with a cozy armchair placed nearby. Large windows allow natural light to fill the room, highlighting the airy layout that connects to the dining area and kitchen.

5 out of 5 average rating, 3 reviews

Modern Comfort Timeless Charm | Log Cabin Retreat

4.95 out of 5 average rating, 63 reviews

A serene outdoor space features a crystal-clear pool surrounded by lush greenery and soft landscaping. Lounge chairs and a bright orange umbrella provide comfortable seating, while the area also includes a hot tub for relaxation. A wooded backdrop adds to the peaceful setting.

Home in Montgomery

Hudson Valley Home with Pool & Jacuzzi

5 out of 5 average rating, 9 reviews

Home in Wurtsboro

Victorian Catskills Retreat—90 min from NYC

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Private house rentals

4.98 out of 5 average rating, 95 reviews

Home in Goshen

Unique Dutch Barn in the Hudson Valley

4.93 out of 5 average rating, 225 reviews

Home in Wappingers Falls

Tranquil Tree-House on the beautiful Hudson River

4.95 out of 5 average rating, 43 reviews

A vibrant display of purple flowers stands prominently in the foreground, with a charming blue house partially visible in the background. Lush green grass surrounds the property, and tall trees can be seen in the distance, creating a serene natural setting.

Home in Wurtsboro

The Alexandria - Wurtsboro, NY

A living area features a green couch paired with a white upholstered chair and a glass side table. A wooden chest serves as a coffee table, while a spiraling wooden staircase leads to an upper level. Natural light enters through large windows, illuminating the space.

4.92 out of 5 average rating, 65 reviews

Warwick Retreat Fireplaces Hot Tub Outdoor Lounge

5 out of 5 average rating, 25 reviews

Home in Greenwood Lake

Lakeview House ~ Hot Tub, Firepit, Stunning Views

5 out of 5 average rating, 5 reviews

The kitchen showcases a blend of modern and vintage design elements. Dark cabinetry is complemented by a striking ceiling featuring patterned wallpaper. Counter space is provided by a central island, with a black refrigerator and stove visible in the background. Warm lighting is offered by a pendant light.

Home in Eldred

Stylish river town escape with hot tub + fire pit

5 out of 5 average rating, 11 reviews

A two-story home with a light-colored exterior and burgundy shutters is set against a clear blue sky. The well-maintained lawn features manicured shrubs and trees, enhancing the inviting curb appeal. The entrance is framed by steps leading to the front door, creating an approachable feel.

Home in Chester

4 Bedroom Home with Hot-Tub