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House vacation rentals in Woodbury

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Quick stats about house rentals in Woodbury

  • Total vacation rentals

    Explore 20 vacation rentals in Woodbury

  • Nightly prices starting at

    Woodbury vacation rentals start at ﺩ.ﺇ 294 per night before taxes and fees

  • Verified guest reviews

    Over 270 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Woodbury vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Woodbury rentals

  • 4.9 Average rating

    Woodbury stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated house rentals in Woodbury

Guests agree: these houses are highly rated for location, cleanliness, and more.

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Guest favorite
A contemporary two-story home is presented, featuring a combination of wood and gray siding. Stone steps lead to an inviting entrance, while surrounding greenery provides a natural backdrop. Large windows allow for ample natural light, enhancing the exterior's modern design.
Home in Highland Falls

Modern 3BD West Point USMA House w/ HotTub!

Our beautiful 3 bed, 2 bath contemporary home sits just 0.4 miles from West Point Military Academy. The house is equipped with super fast internet, work stations in each bedroom, cozy nectar mattresses, a 4-person jacuzzi, and of course, an incredible back yard patio with a BBQ, fire pit and outdoor dining area. Our kitchen is stocked for coffee lovers with 3 different types of machines ( Nespresso, Keurig, and Miele). There are also Samsung Smart TV's in each bedroom along with Sonos speakers!

4.99 out of 5 average rating, 116 reviews
Superhost
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.
Home in Newburgh

Entire Home, Private Indoor Pool

This unique specious and tranquil getaway private home includes an indoor heated swimming pool, hot tub, an outdoor space of 34 acres for you to enjoy nature, work out equipment, movie theater. Complete eat in kitchen, outdoor grill. washer and dryer, three bathrooms. Huge open space basement equipped with LED changing color light. Rooms have Wi-Fi LED light to connect music. The place sleeps 8 guests, in beds. Two additional twin mattresses.16 guests maximum. Hot tub take a while to heat up.

4.81 out of 5 average rating, 136 reviews
Superhost
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

Serene Private Home • Light-Filled • Hot Tub •Deck

Spacious 3,600 sq ft home designed for comfort and ease in upstate New York 🌿 Light-filled rooms, open flow, and a hot tub + deck create a calm, elevated stay ✨ An open layout with multiple living areas makes it easy to gather while still having space to relax and unwind & enjoy throughout. The space functions as a self-contained part of a larger property, offering privacy and independence without feeling segmented. A comfortable base near farms, villages, dining, and outdoor activities.

4.92 out of 5 average rating, 170 reviews
Top guest favorite
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

4.99 out of 5 average rating, 191 reviews
Top guest favorite
A spacious outdoor area features a modern pool surrounded by wooden decking. Lounge chairs are positioned under large umbrellas, providing shade. The two-story home is visible in the background, showcasing large windows that enhance natural light.
Home in Putnam Valley

Heated Pool, Ultra Modern Home 5B, hot tub, sauna

Secluded, luxurious 5Br/3.5Bth home an hour from NYC, nested on a 9-acre property with the Appalachian trail running through. Modern-rustic design, floor-to-ceiling windows, custom kitchen, state-of-the-art appliances, balconies. Dip in the heated pool (seasonal) or the hot tub, sauna, dine alfresco from the BBQ and watch the stars. Guests can enjoy morning coffee on the private deck or evening cocoa in front of the wood-burning fireplace or the fire pit, outside, overlooking a private pond.

4.98 out of 5 average rating, 177 reviews
Top guest favorite
Home in Greenwood Lake

Panoramic Lakeviews & Lush Garden | Beach Access

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

5.0 out of 5 average rating, 227 reviews
Guest favorite
Home in New Windsor

Historic Cornwall Farmhouse w/ Sauna & Hot Tub

Welcome to The Storm King Farmhouse! Experience the best of upstate living in this beautifully renovated 1800s farmhouse located 50 mi from NYC. The property features a heated pool, Finnish sauna, premium hot tub, pickleball & basketball court, fire pit, pond, and more! Located close to exciting Hudson Valley activities - Storm King Art Center (1 min), West Point (15 min), Legoland (25 min), hiking trails, breweries, etc. This is the perfect place to relax with family & friends! Pet friendly!

5.0 out of 5 average rating, 107 reviews
Guest favorite
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.

4.87 out of 5 average rating, 224 reviews
Top guest favorite
A classic blue farmhouse with white trim has a symmetrical facade featuring double-hung windows and green shutters. The entrance is marked by a red door, flanked by two matching red containers. A spacious lawn surrounds the structure, accentuating its inviting presence.
Home in Chester

The Little Green Farmhouse

Built in the mid 1800s, this 2,400 square foot. 2 story farmhouse is a comfortable country getaway with space for the whole family. Nestled on 2.5 acres, the house is perfectly positioned between the villages of Warwick and Sugar Loaf. There are 4 bedrooms on the 2nd floor with the ability to sleep 8 people. There are also 2 full bathrooms, a dining room, living room, office space, fully equipped kitchen, and a bonus space with a table to play board games, cards or puzzles.

4.98 out of 5 average rating, 165 reviews
Top guest favorite
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.

4.99 out of 5 average rating, 210 reviews
Top guest favorite
The exterior of a historic home is showcased, featuring a covered wrap-around porch adorned with patriotic bunting and seating. The interior displays a modern kitchen with granite countertops and stainless-steel appliances, a cozy living room with a comfortable seating area, and a stylish dining space set for six.
Home in Highland Falls

Top-Rated West Point 3 Bed 2 Bath Walk to Thayer

Welcome to the West Point Grad Mom House — Whether you’re visiting your Plebe, Yearling, Cow or Firstie our home was designed with West Point families in mind just steps from Thayer Gate. Why families love staying here: • Walk to Thayer Gate, Main Street • Easy access to West Point • Spacious gathering areas • Historic charm combined with modern comfort • Thoughtful touches from a fellow Grad Mom who understands how special these visits are

5.0 out of 5 average rating, 106 reviews
Superhost
An outdoor space features a circular fire pit surrounded by four wooden chairs. The grass is trimmed, and a deck is visible in the background, providing a cozy area for gatherings. Trees are scattered around the yard, contributing to the natural setting.
Home in Highland Falls

Cozy House 3 Blocks From West Pt

Welcome to this thoughtfully remodeled Historic 1890s home, just steps away from West Point's Thayer Gate. The house is conveniently situated right by Thayer Gate (3 blocks) where there are shuttles to all events and destinations. Steps away (1 block) from the restaurants on Main street and the West Point visiting center and Museum (3 blocks). 10 Mins to Bear Mountain State Park 15 Mins to Storm King Art Center 20 Mins to Woodbury Commons

4.93 out of 5 average rating, 178 reviews

Popular amenities for Woodbury house rentals

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Guest favorite
A scenic view from the steps leading down to the backyard, showcasing a heated pool surrounded by a fenced patio and a newly installed hot tub. Lush green lawn and vibrant flowers complement the serene lake visible in the background, providing a tranquil outdoor atmosphere.
Home in Monroe

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

4.96 out of 5 average rating, 141 reviews
Top guest favorite
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

4.95 out of 5 average rating, 179 reviews
Guest favorite
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

4.88 out of 5 average rating, 243 reviews
Guest favorite
A spacious home theater features seven adjustable faux leather seats arranged in front of a large smart LCD HD TV. Ambient lighting enhances the cozy atmosphere, while a console table is positioned nearby, creating an inviting space for movie nights.
Home in Florida

Legoland Mt Peter 3BR Pool Theater Hot Tub 1Pet

4.96 out of 5 average rating, 108 reviews
Guest favorite
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

4.88 out of 5 average rating, 222 reviews
Guest favorite
Home in Beacon

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

4.92 out of 5 average rating, 181 reviews
Top guest favorite
A spacious living area features large windows allowing natural light to fill the room. A stone fireplace is prominently placed against a wooden wall. Comfortable seating arrangements include a large sectional sofa, with decorative plants adding a touch of greenery.
Home in Yorktown Heights

Cozy getaway 1 hr from NYC!

4.91 out of 5 average rating, 186 reviews
Top guest favorite
A serene outdoor space features a heated saltwater pool surrounded by a spacious lawn. Sun loungers are positioned near an umbrella for shade, with lush greenery and a wooden fence creating a tranquil backdrop.
Home in Pound Ridge

Peaceful Light-Filled Guesthouse salt pool/sauna

5.0 out of 5 average rating, 191 reviews

Weekly house rentals

Guest favorite
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

4.94 out of 5 average rating, 144 reviews
Guest favorite
The lakeside property features a well-manicured lawn leading to the water's edge, complemented by a dock and a single kayak. Lounge chairs are arranged near a shaded gazebo, with a stone pathway guiding guests towards the house, which is framed by lush greenery.
Home in Greenwood Lake

Luxury Lakefront w/ Beach, Dock & Kayak • 1h NYC

4.97 out of 5 average rating, 117 reviews
Guest favorite
A Mediterranean style house is showcased against a backdrop of rolling hills and the Hudson River. The exterior features multiple windows, and a stone chimney rises from the roof. The expansive landscape is highlighted by autumn foliage, creating a vibrant setting.
Home in Garrison

Hudson Valley Mountaintop Riverview

4.93 out of 5 average rating, 185 reviews
Top guest favorite
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.
Home in Cornwall-on-Hudson

Charming Hudson Valley Home: Minutes to West Point

4.96 out of 5 average rating, 142 reviews
Top guest favorite
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!

4.99 out of 5 average rating, 104 reviews
Top guest favorite
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.
Home in Newburgh

The Little Red House

4.99 out of 5 average rating, 159 reviews
Guest favorite
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.
Home in Cornwall-on-Hudson

Cozy Riverfront Victorian in the Hudson Valley

4.92 out of 5 average rating, 194 reviews
Top guest favorite
A single-story home in a vibrant pink hue showcases a unique oval front door, flanked by dark shutters. A concrete pathway leads to the entrance, surrounded by a well-maintained green lawn and partial wooden fencing in the background.
Home in Peekskill

Charming Home in Peekskill NY

4.97 out of 5 average rating, 127 reviews

Private house rentals

Guest favorite
A mid-century octagonal house is surrounded by lush greenery, featuring large glass windows that offer generous natural light. A wooden deck extends from the entry, framed by a black railing. The serene hilltop location provides a peaceful retreat in nature.
Home in New Windsor

View House

4.92 out of 5 average rating, 157 reviews
Top guest favorite
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.
Home in Philipstown

Creekside Home Near Cold Spring & West Point

4.94 out of 5 average rating, 144 reviews
Guest favorite
The exterior of the house is set among lush greenery and features a large elevated deck that wraps around the structure. Large windows provide natural light, and the building is supported by a prominent boulder, blending harmoniously with the surrounding forest.
Home in Ossining

Lower Hudson Valley Idyllic Retreat

4.84 out of 5 average rating, 170 reviews
Top guest favorite
A sunlit seating area features light-colored, oversized chairs and a round coffee table. Large sliding glass doors open to a view of the forest, enhancing the connection to nature. A minimalistic pendant light hangs elegantly above, while a decorative plant adds a touch of greenery.
Home in Cold Spring

Hilltop Hideaway Forest Villa on 13 acres!

4.95 out of 5 average rating, 369 reviews
Top guest favorite
The exterior of the carriage house features a well-maintained garden with lush greenery and a stone path leading to the entrance. Tall trees and shrubs provide a sense of privacy, while a covered porch with swings offers a comfortable place to relax.
Home in Warwick

Historic Village Carriage House Walk to Downtown

4.91 out of 5 average rating, 173 reviews
Top guest favorite
The exterior of the house showcases a modern rustic design, featuring a stone and wood façade. Large picture windows reflect the surrounding nature, while an outdoor fire pit is surrounded by several Adirondack chairs on a grassy area. A dining table and chairs are positioned nearby.
Home in Rhinebeck

Eagle Rock House

5.0 out of 5 average rating, 267 reviews
Guest favorite
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)

4.93 out of 5 average rating, 67 reviews
Top guest favorite
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 Cornwall

Sunset House: near West Point, Hiking & Woodbury

4.98 out of 5 average rating, 59 reviews

Destinations to explore