House holiday rentals in West Point

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, 118 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!

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, 102 reviews

West Point Mountain House

Welcome to West Point! Enjoy early check-in in and late check out at our beautiful mountainside house overlooking the village on its own private hill! Spacious, yet cozy, this house is great for large families or groups of friends coming to explore West Point, Bear Mountain, Storm King, or the Hudson Valley at large. Just 1 hour from NYC and minutes away from restaurants and local attractions. This 3500 Sq Ft home features fun for everyone in a private setting, yet still close to all the fun

A well-maintained front yard features a vibrant array of flowers, including pink and yellow blooms. Neatly trimmed bushes and a white fence enhance the inviting appearance of the farmhouse. The porch is visible, providing a pleasant outdoor space that complements the lush landscaping.

4.97 out of 5 average rating, 119 reviews

Ultimate Walking Access to Thayer Gate USMA

Enjoy the Ultimate Walking Access to Thayer Gate from this Beautiful Farmhouse. Fully immerse yourself in the West Point experience! Hosted by a ‘23 Old Grad Mom, this Beautiful Farmhouse greets you with spacious dining room seating for 10 to gather around the table, fully equipped kitchen with granite countertops for all cooking needs, 75” SmartTV, 350 Roku channels, Cold AC and great backyard for entertaining! Allergen free environment. No smoking or pets. No exceptions or loss of deposit.

4.98 out of 5 average rating, 112 reviews

A lakeside retreat is showcased, featuring a rustic exterior with dark wood accents. Adirondack chairs are arranged near the water's edge, alongside colorful kayaks resting on the peaceful lake. Lush greenery surrounds the property, reflecting in the calm water.

Home in Putnam Valley

Waterfront Lake House

Welcome to your lakeside retreat! Escape to tranquility and breathtaking views with our unique lakefront Airbnb. Nestled right into the water of Lake Peekskill, our cozy lake house promises the ultimate getaway. Adventure awaits right outside your door! Take advantage of complimentary paddleboard or kayaks for a leisurely paddle on the lake. Located just minutes from renowned hiking trails and delicious dining options, our Airbnb offers the perfect balance of serenity and convenience.

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.

4.87 out of 5 average rating, 129 reviews

Lady Montgomery

Enjoy our 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 that the Hudson Valley has to offer. Enjoy shopping, farms,hiking or dining. Equipped with an outdoor patio, fireplace, fire pit and 2 bikes for exploring the area. Everyone will enjoy their time in this comfortable artsy home!

The exterior of a historic Gothic Victorian house displays a charming white façade with detailed gables and a covered front porch. Lush green lawns and trees surround the property, while a shaded outdoor seating area under a red umbrella adds to the inviting ambiance.

4.93 out of 5 average rating, 181 reviews

Cozy Riverfront Victorian in the Hudson Valley

Wake up to stunning views of the Hudson River in this huge, immaculately clean, & beautifully designed historic home. Welcome to Sparrow House, our one-of-a-kind 1859 Gothic Victorian in the Hudson Valley. Only 80 minutes from NYC, 19 minutes away from the Beacon stop on the Hudson line/Metro-North, and 13 minutes from the Salisbury Mills/Cornwall Stop on the Port Jervis line/NJ Transit. The house is spacious, has exquisite light, and river and mountain views from nearly every room.

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.

4.86 out of 5 average rating, 146 reviews

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

All About "Mitzi" Clean 2-story house on a residential street/safe area Free on-off street parking Eat-in kitchen Dining room Living room-fold out ottoman Free washer-dryer 2 Internet TVs, WIFI Work area Large backyard, art supplies, games, books Fire pit NEW Community Pool-walking distance Close to West Point, Storm King, the Hudson, Woodbury Mall, hiking, restaurants, bars, shopping No river or mountain view directly from house (per ABnB) BRAND NEW PLUMBING

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, 134 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

A wooden exterior house is surrounded by trees displaying autumn foliage. A pathway of stones leads to the entrance, where a deck with white railings is visible. Lush shrubs and decorative rocks enhance the natural landscaping.

4.94 out of 5 average rating, 143 reviews

Cozy 3 bedroom house on quiet private road

3 bedroom house overlooking creek on a quiet, private road. Minutes from Hudson Valley Shakespeare, Metro North Railroad, Hudson River, historic Cold Spring Village, Highlands Country Club golf course, Beacon, downtown Peekskill, Bear Mountain State Park, Boscobel House & Gardens, Fahenstock St Park and West Point Military Academy. Restaurants, farmer’s markets, hiking trails. We are dog friendly but there is an additional fee of $80 per stay.

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, 193 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!

The living room features a combination of a black sofa and a light gray couch, adorned with red accent pillows. A wooden coffee table is positioned in the center, and light from a nearby window illuminates the space, complemented by a ceiling fan and wall-mounted television.

4.81 out of 5 average rating, 127 reviews

Lovely 3BR Home with parking-Walk to WP Gate!

Walk to West Point! Enjoy the Hudson Valley. Bring the whole family to this great place with lots of room for fun. Cozy up in our spacious living room while dinner is cooking in the fully equipped kitchen. The back deck is perfect for morning coffee, unwinding in the evening with a glass of wine or a family BBQ. You will find everything you need for work or play here in the heart of Highland Falls, New York. Looking forward to having you!

A charming blue house features a welcoming front porch with steps leading up to the entrance. White shutters adorn the windows, and flower boxes add color. A flag is displayed in front, with a well-maintained lawn and greenery surrounding the property.

4.96 out of 5 average rating, 140 reviews

Charming Hudson Valley Home: Minutes to West Point

Located in the Lower Village of Cornwall on Hudson, 5 miles from West Point, 4 miles from Storm King Arts Center and minutes from amazing hiking trails. This charming house offers everything you need for a relaxing getaway. Spacious deck makes it the perfect spot for a relaxing evening outside. The beautiful Hudson Valley and this charming house can't wait to welcome you! **Home does not have a washer/dryer available

Popular amenities for house rentals in West Point

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.98 out of 5 average rating, 528 reviews

An in-ground swimming pool is surrounded by lush greenery, offering a serene outdoor escape. Lounge chairs are positioned on the pool deck, inviting relaxation. The area is accented by planters, creating an inviting and enjoyable outdoor space.

Home in New Paltz

midcentury mod * POOL * walk out trail 2 mohonk

4.81 out of 5 average rating, 90 reviews

A private outdoor pool is surrounded by lounge chairs and umbrellas, offering a perfect spot for relaxation. Lush greenery borders the area, enhancing the tranquil environment. A small shed is visible in the background, providing additional charm to the outdoor space.

Home in Highland Mills

A Premium Hudson Valley Retreat 60-75min from NYC

4.81 out of 5 average rating, 165 reviews

An expansive outdoor area features a private pool surrounded by lush greenery. Shade is provided by colorful umbrellas over seating arrangements. A custom-built outdoor kitchen is visible, along with a bar seating space. The paved patio offers ample room for relaxation and entertainment.

Home in Goshen

The Getaway, Pool, Hot Tub, Lego Land, Arcade

4.87 out of 5 average rating, 208 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

4.94 out of 5 average rating, 78 reviews

Hudson Riverview Retreat

An outdoor pool area features a stone patio surrounded by vibrant flowers and greenery. Lounge chairs are arranged neatly beside the pool, and a wooden cabana is visible with a stone fireplace, creating a relaxing atmosphere for guests.

4.87 out of 5 average rating, 87 reviews

Gorgeous Garrison Gem Sauna, Spa 5 min Cold Spring

4.98 out of 5 average rating, 115 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

4.92 out of 5 average rating, 165 reviews

Home in Beacon

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

Weekly house rentals

4.98 out of 5 average rating, 55 reviews

The living room features two navy blue sofas positioned across from each other, creating a welcoming conversation area. A glass coffee table is centered on a light-colored carpet. Natural light filters through sheer curtains, highlighting views of the surrounding greenery.

Home in Mountainville

Sunset House: near West Point, Hiking & Woodbury

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, 19 reviews

West Point Family Retreat 5 min walk to Thayer

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, 41 reviews

Margaret's Heart

4.93 out of 5 average rating, 58 reviews

A cozy outdoor gathering space is depicted, featuring a wooden gazebo with a stone firepit at its center. Surrounding seating is illuminated with soft lighting, enhancing the inviting atmosphere. Pathway lights line the walkway, leading to lush greenery in the background.

Home in New Windsor

2-Queen 1-Twin 2-Bath Home West Point/Low-Hud Area

5 out of 5 average rating, 24 reviews

Old Grad House, within Cadet Walking Privileges

4.85 out of 5 average rating, 13 reviews

Delightful Home!

5 out of 5 average rating, 23 reviews

Modern, sun-filled farmhouse retreat

4.93 out of 5 average rating, 55 reviews

A comfortable living area is created with two armchairs positioned around a circular glass table. A wood-burning fireplace adds warmth, with flames visible in the hearth. Natural light filters through the window, highlighting a modern kitchen bar with high stools in the background.

Home in Monroe

3 BDR Cottage (Hudson Valley Cottage)

Private house rentals

4.94 out of 5 average rating, 62 reviews

Home in Cold Spring

Cottage in the village of Cold Spring

A concrete pier extends over the tranquil water, featuring two lounge chairs positioned for relaxing views of the river and surrounding landscape. Lush greenery and distant homes are visible across the water, enhancing the peaceful outdoor setting.

4.73 out of 5 average rating, 174 reviews

Bungalow near West Point on Hudson River

4.98 out of 5 average rating, 42 reviews

A two-story house features a green exterior with a prominent red front door. Solar panels are arranged on the roof, and a welcoming porch with white railings invites relaxation. The backdrop showcases a serene landscape with bare trees, illuminated by a soft sunset sky.

Home in Cornwall

Cozy Cornwall Retreat Near Hudson Valley

5 out of 5 average rating, 82 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!

4.92 out of 5 average rating, 24 reviews

An aerial view of a contemporary home nestled among greenery, showcasing a spacious wraparound deck with outdoor seating. The property features a manicured lawn, gardens with blooming plants, and a paved entrance leading to the driveway.

Home in Mountainville

Hudson Valley Hideaway: 10 Minutes to Storm King!

5 out of 5 average rating, 19 reviews

A cozy living area is furnished with a variety of seating options, including a blue sofa and two armchairs. A wooden coffee table sits in the center on a textured area rug. A flat-screen TV is mounted on the wall, accompanied by a window bringing in natural light.

Home in New Windsor

Charming Farmhouse Getaway and Hot Tub

4.99 out of 5 average rating, 68 reviews

A single-story cottage is shown surrounded by lush greenery. Solar panels are installed on the roof. The entrance features a small set of stairs leading to a front porch with steps flanked by shrubs. Red shutters accentuate the windows, offering a welcoming appearance.

Home in Cold Spring

Mountain Top Retreat

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.