House vacation rentals in Middletown

4.94 out of 5 average rating, 338 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.

4.96 out of 5 average rating, 157 reviews

A modern living space features an artificial green wall, providing a natural feel. A sleek stone fireplace sits below a mounted flat-screen TV, which displays a serene sky. Soft seating options create a comfortable area for relaxation.

Home in West Milford

The Wine & Wilderness Hideaway [Cal King •1hr NYC]

*COZY UP IN OUR SPRING OASIS NOW! Nature’s haven, indulge in seamless spacious single-level living! Minutes away from Mountain Creek Spa & Water park, Warwick wineries, breweries, creameries & apple picking, scenic hiking trails, serene lakes, enchanting parks, & indulgent restaurants. Open concept, Chef's kitchen, Dishwasher, Washer & Dryer, 2 BR, 2 Bath, Cal King bed w primary BR attached to private Bath w soaking tub a retreat to relaxation. Huge patio & fireplace create everlasting memories

4.91 out of 5 average rating, 169 reviews

The exterior of the lake house is shown, featuring a blue facade with white trim. A small front deck with steps leads to the entrance. Lush greenery surrounds the property, providing a serene backdrop. A gravel path leads up to the house, enhancing a rural feel.

Home in Rock Hill

Beaver Lake Escape

Welcome to Beaver Lake Escape! This one bedroom, one bathroom lakeview home has all of the amenities you will need for a relaxing vacation getaway! Come experience a warm & cozy environment with full access to the community beach where you can enjoy kayaking, swimming and fishing (catch & release). You'll also find great hiking in the Spring, Summer and Fall at the Neversink Gorge Unique Area and skiing/snow boarding in the winter at Holiday Mountain! Only a 25 minute drive to Bethel Woods!

4.99 out of 5 average rating, 189 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, 141 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.

4.88 out of 5 average rating, 156 reviews

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

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.

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.

4.98 out of 5 average rating, 188 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.

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.

4.99 out of 5 average rating, 161 reviews

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.

Home in Warwick

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

4.95 out of 5 average rating, 128 reviews

A spacious living room features royal blue couches surrounding a central coffee table. Natural light floods the area through large sliding doors and a skylight, highlighting a brick accent wall and a fireplace. A decorative plant adds a touch of greenery.

Home in Chester

Millionaire Mansion Countryside Stay w/ Lrg Hottub

You'll be staying in a millionare mansion in the town where cream cheese was invented. Immerse in the fresh upstate NY nature nearby farms! Sugarloaf antique village, famous vineyards, luxury shopping, amusement parks, hiking, swimming, and restaurants. Surround yourself with mountain views through floor-to-ceiling windows spilling shimmering light into spacious rooms. Every room flows effortlessly into the next, naturally creating the space for deep connections.

4.93 out of 5 average rating, 223 reviews

A serene view of the Hudson River at sunset, with vibrant colors reflected in the water. A silhouetted tree stands in the foreground, while the sky is adorned with clouds that capture shades of orange and purple, enhancing the tranquil atmosphere of the surroundings.

Home in Wappingers Falls

Tranquil Tree-House on the beautiful Hudson River

Take it easy at this unique and tranquil getaway. Be our guest at our beautiful home located on the widest part of the Hudson River. Enjoy a private room with a queen size bed and a large screen smart tv. The full bathroom is located across the hallway. Enjoy a warm fire in the sitting area. There is a work area and a high table to enjoy some tea/coffee or wine with dinner while enjoying the view of the Hudson through the large windows and sliding door.

4.91 out of 5 average rating, 185 reviews

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

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

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Cabins

Kick off your hiking boots at these rustic lodgings

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Middletown house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.94 out of 5 average rating, 182 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

4.98 out of 5 average rating, 147 reviews

Home in Effort

Villa in the Sky - Best View of Pocono Mountains!

4.86 out of 5 average rating, 159 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, 251 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

4.92 out of 5 average rating, 156 reviews

Home in East Stroudsburg

Sauna | Movie Theater | Hot Tub | Dogs OK |Firepit

4.88 out of 5 average rating, 262 reviews

A spacious living area features a stone fireplace and large windows overlooking Lake Larsen. Comfortable seating is arranged on warm wooden floors, leading to an inviting outdoor deck with a dining table and umbrella. Natural light enhances the relaxing ambiance.

Home in Gouldsboro

Lake Front Retreat in the Poconos * King Bed*

Home in Lackawaxen Township

5 out of 5 average rating, 110 reviews

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

4.95 out of 5 average rating, 202 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

Show all

Weekly house rentals

4.91 out of 5 average rating, 47 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

5 out of 5 average rating, 117 reviews

Home in Parksville

The Catskill Getaway • Near Bethel Woods & Hiking

4.97 out of 5 average rating, 62 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

4.99 out of 5 average rating, 88 reviews

A circular stone patio surrounds a central fire pit, featuring six red Adirondack chairs. The modern house with a welcoming entrance is partially obscured by lush green trees in the background, creating a natural and serene environment.

Home in Montgomery

Modern Woodland Retreat, Hudson Valley & Catskills

4.95 out of 5 average rating, 41 reviews

A private deck with a dining table and six chairs overlooks a serene lake, framed by a vibrant backdrop of autumn foliage. The wooden deck features a spacious layout, inviting guests to enjoy outdoor meals while surrounded by nature.

Home in Pine Bush

Cabin96-Shawangunk Mountain View

A serene lake reflects the surrounding greenery, with lush grass and wild plants at the water's edge. The calm surface mirrors a partly cloudy sky, creating a peaceful natural scene ideal for relaxation and outdoor exploration.

4.92 out of 5 average rating, 12 reviews

Lake trail retreat

4.96 out of 5 average rating, 312 reviews

The image captures the exterior of a modern home, showcasing its wooden facade alongside natural elements. Tall trees stand near the structure, with a gravel base visible at the bottom. The design reflects a strong connection to the surrounding woodland environment.

Home in Kerhonkson

Architect's Hudson Valley Home in the Woods

The exterior of Wawayanda Lodge is presented, featuring a modern one-story house with a combination of stone and white siding. The landscape includes green grass and a few trees, while the spacious driveway allows ample parking. Windows provide natural light to the interior.

4.95 out of 5 average rating, 78 reviews

Wawayanda Lodge - Port Jervis, Hudson River

Show all

Private house rentals

4.76 out of 5 average rating, 93 reviews

A wooden deck features a pair of wrought-iron chairs and a small table, offering a serene outdoor space. Lush greenery surrounds the area, with tall trees providing shade and hills visible in the distance under a partly cloudy sky.

Home in Mountain Dale

little cozy house in the village

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.

4.81 out of 5 average rating, 26 reviews

Country Modern Home w/5-Acre land Relax Retreat

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.

4.9 out of 5 average rating, 96 reviews

Hudson Valley Log Cabin with Lake Access & View

4.95 out of 5 average rating, 42 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

5 out of 5 average rating, 85 reviews

An open living area features a modern kitchen with dark cabinetry, a central island, and stainless steel appliances. A cozy seating arrangement includes a leather sofa, a wooden coffee table, and a stylish rug. Large windows allow natural light to fill the space, connecting to the outdoors.

Home in Warwick

Beautiful Summer Warwick Escape! New Home!

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

4.85 out of 5 average rating, 46 reviews

A white brick fireplace acts as a focal point in the spacious living room. The fire burns brightly inside the hearth, surrounded by built-in wooden shelves filled with plants and decorative items. A potted plant is positioned to the left, adding greenery to the space.

Home in Woodridge

The First House