House vacation rentals in Highland Falls

Home in Cornwall-on-Hudson

A two-story white house is framed by lush green trees. The front porch features red rocking chairs and hanging flower baskets. An American flag is displayed on the porch. A pathway leads to the entrance, which is highlighted by white railings and steps.

4.99 out of 5 average rating, 113 reviews

Your West Point Academy Home Away from Home

Make yourselves at home in this lovely, privately-owned residence as you attend West Point Academy events and tour scenic Hudson Valley. Build in 1900 and renovated in 2019, this house combines historic charm (original wood floors) with modern conveniences. The home's location is a twelve-minute drive to West Point's Washington Gate and within walking distance to the restaurants and shops of Cornwall. Enjoy 4th of July fireworks and weekly summer concerts with ease relaxing on the front porch!

4.96 out of 5 average rating, 257 reviews

A charming two-story house features warm wooden siding and multiple red window accents. A welcoming front porch is adorned with lights, complemented by a gently sloped pathway leading up to the entrance, surrounded by lush greenery and seasonal foliage.

Home in New Paltz

Eclectic one-bedroom house

This bohemian New Paltz house is 1/3 mi to Main St New Paltz, 2/3 mi to SUNY and 1 1/2 blocks from the New Paltz-Kingston rail trail. Rent entire house with a private bathroom, large deck space with table and grill, small living and dining room, EV charging and a kitchen. The entire upstairs is a spacious and unique bedroom space. Walking distance to many restaurants and bars. New Paltz is a central location for outdoor fun, close to Mohonk, the Gunks, great biking, hiking, rock climbing, etc.

4.99 out of 5 average rating, 132 reviews

A hammock is suspended between two trees, providing a relaxing spot beside the lake. Vibrant autumn leaves in shades of orange and yellow frame the serene water view, while a wooden dock is visible in the background, inviting guests to enjoy the tranquil setting.

Home in Putnam Valley

Luxury Lake House Sauna 1h From NYC

Enjoy the lakefront from my charming home! Fish or Kayak from the private dock or relax on the large deck overlooking the water tucked away on the lake. Boats are included for all guests! Heated bathroom floors, massive TV (86in) + ample lake views. We also have a free Tesla Charger (with an adaptor you can use for other EVs). This is a relaxing retreat tucked away in one of New York's most convenient lakefronts from the city. 20 min to Bear Mountain 35 min to West Point 1 hour to NYC

Home in Cornwall-on-Hudson

A two-story house is situated on a quiet residential street, featuring a white exterior with a contrasting brick foundation. The entrance is framed by multiple windows, allowing natural light to illuminate the interior. A well-maintained yard with greenery surrounds the property.

4.87 out of 5 average rating, 141 reviews

Eclectic, Sleeps 5, Wsher/Dryer, Parking, Yard, AC

"Mitzi" is a clean 2-story house on a quiet residential street/safe area. Eat-in kitchen, dining room, 2 twins, one queen, fold out bed in Living Room, shower/tub, washer/dryer, dedicated work area, Internet TV&ROKU, 2 flrs, large backyard, sml bbq, fire pit, many art supplies, games, books. Free on/off-street parking. Close to West Point, Storm King, the Hudson, Woodbury Mall, hiking, restaurants, bars, shopping. Town pool easy walking distance. No river or mountain view directly from house.

A charming two-story house is featured with a light yellow facade and white trim. A welcoming front porch with a bench overlooks the neatly landscaped yard, filled with greenery and flower beds. The inviting entrance is flanked by large windows and decorative shutters.

4.86 out of 5 average rating, 113 reviews

Lady Montgomery

Enjoy this trendy and comfortable home overlooking the Hudson river. Lady Montgomery is set in the perfect family-friendly neighborhood, walking distance to the bridge trail to Beacon and Newburgh waterfront. Perfect for friends and couples who want to explore all the Hudson Valley has to offer like shopping, hiking or dining. Equipped with an outdoor patio, fire pit and two bikes to help you explore the surrounding areas. Everyone will enjoy their time in this comfortable artistic home

4.98 out of 5 average rating, 120 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!

4.95 out of 5 average rating, 174 reviews

A spacious living area is centered around a stone fireplace, adorned with wood beams. Natural light filters through large glass doors, offering views of the greenery outside. Comfortable couches are positioned invitingly, creating a relaxing atmosphere for guests.

Home in Cold Spring

Cozy, Modern Retreat in the Woods of Cold Spring

Newly renovated with modern style and amenities yet retaining all of its rustic warmth and charm, our home is perfect for your next get away. Outdoors, enjoy the salt water pool, patio, grill and fire pit in our secluded setting. Indoors we offer a sauna, steam shower, central heat and air, a woodburning fire place, ping pong table, washer and dryer, and a fully loaded kitchen. Located 7 minutes drive from charming Cold Spring and just across the river from West Point.

4.99 out of 5 average rating, 196 reviews

A view of the exterior of the property is framed by lush greenery, featuring a stone wall with a potted plant. Beyond, expansive views of the lake and surrounding mountains are visible beneath a clear sky.

Home in Sterling Forest

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.

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.

4.99 out of 5 average rating, 173 reviews

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.

A charming two-story house features a combination of red siding and stone accents. A welcoming porch with white railings leads to the front door. Lush greenery surrounds the entrance, enhancing the inviting exterior. Nearby, a well-maintained lawn adds to the home's appeal.

4.99 out of 5 average rating, 121 reviews

The Little Red House

Located in a quiet neighborhood just off the Hudson River, yet only a 10 min drive from the bustling town of Beacon and within walking distance to the Newburgh action where you will find restaurants, coffee shops, galleries local shopping, and nightlife. With countless hiking spots, farms, breweries, and wineries, your stay in Hudson Valley will be memorable. The house was also a filming & staging location for the movie “Adults” starring Michael Cera

An open dining area features a wooden table surrounded by six dark chairs. A stylish light fixture hangs above, and a modern kitchen with white cabinetry and stainless steel appliances is visible in the background. Natural light filters through nearby windows.

4.99 out of 5 average rating, 182 reviews

Spacious, bright 5 bedroom house near West Point

Recently renovated 5 bedroom, 2 bathroom house located 4.3 miles from the Thayer Gate at historic West Point Military Academy. Located in the scenic Hudson Valley near hiking, fishing, Bear Mountain State Park and many historic sites.Woodbury Commons premium outlets are 20 minute drive. The house is comfortable with many upgrades- full oven and microwave, large fridge/freezer, USB ports .Come and see an Army game - and relax here afterwards!

4.93 out of 5 average rating, 251 reviews

Home in Wappingers Falls

Tranquil Tree-House on the beautiful Hudson River

Take it easy at this unique and tranquil getaway. I look forward to hosting you. 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.

Popular amenities for Highland Falls house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.94 out of 5 average rating, 196 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, 508 reviews

The exterior of a Mid Century Mod house is showcased at night, illuminated by soft outdoor lights. The building features large windows that reveal glimpses of the interior, while the surrounding lawn is landscaped with grass and scattered fallen leaves.

Home in New Paltz

midcentury mod * HOT TUB * walk out trail 2 mohonk

An indoor heated swimming pool is featured, surrounded by wooden paneling and illuminated by colorful LED lights. A hot tub is positioned beside the pool, with two lounge chairs placed nearby. Large windows offer views of the exterior while maintaining a cozy atmosphere.

4.83 out of 5 average rating, 109 reviews

Entire Home (private pool), Event Friendly

4.89 out of 5 average rating, 166 reviews

A tranquil brook flows through a rocky gorge, surrounded by lush trees and rugged stone formations. The scene showcases the natural landscape, leading toward a wooden deck with a canopy, providing a peaceful retreat in a serene setting.

Home in Rhinebeck

4Br Mountain Brook House on 130 acres w/ trails

5 out of 5 average rating, 172 reviews

The exterior of a charming guesthouse is illuminated during twilight, with warm string lights hanging above a patio area. Large windows reveal the inviting interior, while tall trees frame the scene, creating a serene atmosphere in the evening.

Home in Pound Ridge

Peaceful Light-Filled Guesthouse 1 Hour From NYC

4.98 out of 5 average rating, 111 reviews

The two-story farmhouse features a warm yellow exterior and a large, screened sunroom that extends along the back. A spacious yard is visible, adorned with trees and greenery, while a swing set adds a playful touch to the outdoor area.

Home in High Falls

Cozy & Spacious Country Home - All Seasons

4.91 out of 5 average rating, 150 reviews

A spacious backyard is highlighted by a shimmering in-ground pool surrounded by lounge chairs and cabana umbrellas. Lush greenery frames the area, creating a tranquil atmosphere. A slide is visible in the pool, and a vibrant blue sky with clouds adds to the inviting scene.

Home in Beacon

Beacon Beauty 4/2, Hot Tub,Pool,Wifi,1.5m to Town

4.9 out of 5 average rating, 108 reviews

Home in Grahamsville

Spacious Catskills Farmhouse on over 5 acres!

Weekly house rentals

The living room features a stone fireplace and a large wall-mounted television. Two blue armchairs are positioned next to a light-colored coffee table. A staircase with wooden steps leads to the upper floor, and artwork adorns the walls.

5 out of 5 average rating, 12 reviews

West Point Family Retreat 5 min walk to Thayer

The exterior of a contemporary two-story home is showcased, featuring a combination of gray and wood paneling. The property is situated on a landscaped slope adorned with planters. A set of stone steps leads up to the entrance, framed by greenery and a cloudy sky above.

5 out of 5 average rating, 83 reviews

Modern Usma Home, Walk to West Point. Hot Tub!

5 out of 5 average rating, 99 reviews

A spacious great room features a stone fireplace amidst large windows, allowing natural light to fill the space. A wooden dining table is placed near a comfortable sectional sofa, creating an inviting area for relaxation and dining. The warm wood beams add a rustic touch.

Home in Staatsburg

Boulder Tree House

4.92 out of 5 average rating, 26 reviews

A serene outdoor setting features a sparkling swimming pool surrounded by lush greenery. Comfortable seating areas, including deck chairs, are positioned nearby. Hammocks hang between trees, providing a relaxing retreat. Scenic views of the Hudson River and mountains enhance the tranquil atmosphere.

Home in Philipstown

Arkadia House Mid-century retreat with pool & view

4.94 out of 5 average rating, 67 reviews

A stone patio is shown with six colorful chairs arranged around a fire pit. In the background, trees and a trampoline are visible, contributing to a serene outdoor setting, ideal for gathering and relaxation.

Home in Mohegan Lake

A nice place to getaway

The spacious bedroom features a king bed dressed with neutral linens and a decorative throw. Natural light floods through the large windows, complemented by soft curtains. A seating area includes a comfortable chair, and decorative artwork lines the walls, enhancing the room's charming atmosphere.

4.92 out of 5 average rating, 26 reviews

Sleek Escape: Modern 3 BR- 4 Min from West Point !

4.8 out of 5 average rating, 10 reviews

Charming Apartment in Newburgh

A modern kitchen area is shown, featuring a large wooden dining table with black chairs and sleek bar stools at a kitchen counter. Stylish pendant lights hang above, while a gas range is displayed beside stainless steel appliances. Natural light enters through window treatments.

5 out of 5 average rating, 11 reviews

Our Rockbound Retreat

Private house rentals

A single-story home is presented with a welcoming front porch featuring white columns and a light grey exterior. The porch includes a wooden step entry leading to the front door, surrounded by lush greenery and a gated fence, providing a cozy, private outdoor space.

4.9 out of 5 average rating, 40 reviews

Margaret's Heart

5 out of 5 average rating, 20 reviews

Old Grad House, 850ft from Thayer Gate

The exterior of the house is surrounded by trees, with a welcoming front porch featuring chairs. A circular stone fire pit area is visible in the yard, complemented by a gravel surface and wooden adirondack chairs. The driveway is paved and leads to the garage.

4.97 out of 5 average rating, 93 reviews

West Point Mountain House

5 out of 5 average rating, 25 reviews

Home in Putnam Valley

Fall Splendor at Dr. Ruth’s Lake Retreat

5 out of 5 average rating, 13 reviews

A comfortable living room features a mix of seating options, including a patterned armchair and a bright blue couch. A small wooden coffee table sits at the center, surrounded by an area rug. Natural light enters through large windows, enhancing the space's inviting feel.

Home in Peekskill

Victorian Eclectic

A spacious living area features an elegant chandelier hanging from a wooden beam ceiling. A white chaise lounge and a blue armchair are positioned around a wooden coffee table. Warm light enters through windows, illuminating the colorful area rug that covers the hardwood floor.

4.97 out of 5 average rating, 65 reviews

West Point Hudson Valley Getaway

5 out of 5 average rating, 66 reviews

A charming home nestled among trees features a spacious front porch adorned with planter boxes. Lush greenery and colorful flower beds surround the property, and a large boulder adds a natural element to the landscape.

Home in Cold Spring

Home in Cold Spring- Farm Stay!