House vacation rentals in Middletown

4.94 out of 5 average rating, 345 reviews

A striking landscape features a modern home beside a serene pond. Lush green lawns and colorful trees reflect beautifully in the water. Towering conifers and deciduous trees frame the scene, enhancing the idyllic outdoor setting.

Home in Woodstock

Woodstock Historic Artist Estate - The Pond House

Awaken to an idyllic lake view through a timber-framed glass facade. Acclaimed social realist painter Reginald Marsh's family estate is known to be unique for Woodstock with its ball shaped junipers, a pond that brackets the house, expansive lawns, a gathering of birches and 100 year old cone shaped cedar trees. In short walking distance to the center of Woodstock the secluded setting with a private waterfall bordering a public preserve as well as the attention to architectural detail is unique.

4.94 out of 5 average rating, 132 reviews

A wooden dock extends over the calm water, featuring two lounge chairs facing the serene lake. Lush greenery borders the lake, with rolling hills visible in the background under a partly cloudy sky.

Home in Swan Lake

Bright Lake House with Hot Tub, Kayaks & Firewood

Your next adventure is right around the corner at this cozy New York home. Situated 8 miles from the Historic Site of the 1969 Woodstock Festival. This 2-bedroom, 1-bathroom vacation rental combines serene lakefront living with the exciting sites of the Catskills. Head onto the deck each morning to enjoy a cup of coffee while you take in the stunning views or spend the afternoon kicking back in the hot tub. With its ideal location and impressive outdoor space, this abode is a guaranteed hit!

5 out of 5 average rating, 279 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, 198 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, 143 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.

4.99 out of 5 average rating, 103 reviews

A bright living area is observed, featuring cozy seating arrangements with a mix of chairs and a sofa. A television is mounted on the wall, while sliding glass doors provide views of the surrounding nature. A gas fireplace adds warmth, and a decorative rug enhances the space.

Home in Kingston

Hillside Views in Hudson Valley

Escape to this modern, cozy retreat where nature surrounds you. Fall asleep to owls, crickets, and frogs. Just 2 mins from Rosendale and a short drive to Kingston, New Paltz, and Stone Ridge, with restaurants and trails nearby. Enjoy a gas fireplace, a reading nook with treetop views, and a large deck that feels like you’re in the trees. The private outdoor space includes a fire pit, all on a serene 3-acre lot offering total peace and quiet. Your perfect Hudson Valley escape awaits!

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, 166 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, 194 reviews

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

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, 188 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, 164 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, 165 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.

Superhost

A cozy sleeping area is featured, highlighting a spacious bed with crisp white linens and a gray blanket. A decorative honeycomb shelf hangs on the dark blue wall, providing an artistic accent. Soft lighting enhances the peaceful ambiance.

Home in Goshen

4.91 out of 5 average rating, 191 reviews

Goshen House: hot tub, fenced yard, by downtown

Escape to The Goshen House. Enjoy relaxation, convenience, and open space in our new well-stocked and centrally-located home. This home was designed with comfort in mind: you'll love the radiant heat floors, open floor-plan, and modern kitchen. Let Fido get the zoomies out in the fenced-in yard or take her out on Heritage Trail, just steps away. Or just relax in the zen backyard, including a hot tub, fire pit and grill. Only 1 hour drive to Manhattan.

Vacation rentals for every style

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Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Middletown house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.98 out of 5 average rating, 499 reviews

Home in New Paltz

midcentury mod * HOT TUB * walk out trail 2 mohonk

An aerial view of a house is surrounded by dense green trees, with a clear pool visible in the backyard. The lawn is lush and includes a pathway leading to the pool area, blending harmoniously with the natural landscape.

4.92 out of 5 average rating, 115 reviews

Summer Retreat! Amazing Pool, Playground, 7 acres!

4.98 out of 5 average rating, 244 reviews

The main living area features warm wood beams and a stone fireplace, surrounded by an eclectic collection of wall art. A vibrant coral sofa extends across the room, facing a large television and inviting seating arrangements at the dining table. Natural light flows in through the windows.

Home in East Stroudsburg

4.86 out of 5 average rating, 165 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

4.95 out of 5 average rating, 210 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

4.91 out of 5 average rating, 103 reviews

A serene outdoor space features a saltwater pool surrounded by lush greenery and fencing. Lounge chairs with brightly colored towels are positioned on the stone patio, inviting relaxation alongside the tranquil water.

Home in Saugerties

Stylish Woodstock Pool Home

Superhost

The exterior of a Victorian-style farmhouse is visible, surrounded by lush greenery. A wraparound porch adds architectural interest, adorned with white railings. The sloped roof and multiple gables characterize the charming structure. Pathways lead through the well-maintained gardens, inviting exploration of the natural surroundings.

Home in Grahamsville

4.89 out of 5 average rating, 102 reviews

Spacious Catskills Farmhouse w/ In-Ground Pool!

4.95 out of 5 average rating, 278 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)

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Weekly house rentals

4.98 out of 5 average rating, 99 reviews

Home in Goshen

Unique Dutch Barn in the Hudson Valley

4.97 out of 5 average rating, 66 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

4.96 out of 5 average rating, 45 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

4.94 out of 5 average rating, 16 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, 20 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

Superhost

A light-filled great room features floor-to-ceiling windows and a striking stone fireplace. Rustic wooden beams accentuate the high ceiling, while a plush sofa and vibrant area rug create a cozy ambiance. A dining area is visible in the background, enhancing the spaciousness.

Home in Montgomery

4.73 out of 5 average rating, 40 reviews

The Montgomery Chalet

5 out of 5 average rating, 26 reviews

A charming blue cottage is nestled among dense greenery, featuring a spacious patio with comfortable seating and an umbrella for shade. A barbecue grill is positioned nearby, and large windows reflect natural light, enhancing the inviting exterior surrounded by well-maintained landscaping.

Home in Pond Eddy

Lunar Lounge • 6 acres • Fireplace • Pet Friendly

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, 5 reviews

Modern Comfort Timeless Charm | Log Cabin Retreat

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Private house rentals

5 out of 5 average rating, 75 reviews

A sunlit sun room features large windows offering scenic lake views and a warm wooden ceiling. A cozy, circular seating area complements a central wooden table. Nearby, a dining table with black chairs sits atop a modern area rug, enriching the space's inviting ambiance.

Home in Vernon Township

Private Island + Lakefront Home

5 out of 5 average rating, 13 reviews

A peaceful seating area overlooks a gently flowing river, surrounded by lush greenery and trees. Two comfortable chairs are positioned around a small round table, inviting relaxation and enjoyment of the serene outdoor setting.

Home in Pine Bush

River Ridge House

4.96 out of 5 average rating, 83 reviews

A charming two-story cottage is nestled among trees with autumn foliage. The welcoming front porch features stone walls and a pathway leading to the entrance. A spacious yard is surrounded by grassy areas and decorative rocks lining the driveway.

Home in Matamoras

The Victorian at Bluestone Falls

4.95 out of 5 average rating, 20 reviews

A spacious bedroom features a large bed adorned with plush orange and olive green textiles. A wooden sliding barn door separates adjoining sleeping areas. Soft lighting from modern lamps creates a warm glow, while a stylish desk and chair offer a dedicated workspace.

Home in Liberty

Magical Treehouse Retreat | Pond & Fire Pit

4.93 out of 5 average rating, 59 reviews

A historic colonial farmhouse is presented with a light-colored exterior. A vibrant red door serves as a focal point, complemented by neatly trimmed hedges and blooming flowers. The manicured lawn stretches out in front, enhancing the welcoming entrance framed by multiple windows.

Home in Westtown

Historic Westtown Farmhouse on 18 private acres.

4.97 out of 5 average rating, 31 reviews

The living room features warm wooden floors and exposed beams, creating a cozy atmosphere. A spacious sofa is paired with a modern armchair and side table. A fireplace is flanked by shelves displaying books and decor, while a guitar rests against a wall.

Home in Kingston

NEW: Luxe Historical Style in Stone Ridge.

4.96 out of 5 average rating, 67 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