Pet-friendly vacation rentals in Woodbury

4.99 out of 5 average rating, 112 reviews

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!

Outdoor spacesWalkabilityCleanliness

4.81 out of 5 average rating, 134 reviews

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.

Outdoor spacesPetsGrill

4.86 out of 5 average rating, 235 reviews

A spacious living area features a black leather sofa and an orange ottoman, complemented by a large potted palm. Bright light enters through the open door, enhancing the warm wood flooring and inviting atmosphere.

Apartment in Newburgh

Historic Stunner w/WasherDryer, Balcony, 2 bedroom

Our cozy historical 2 bedroom apartment with river views, two porches, and modern upgrades is just what you need for a delightful getaway or focused work-cation. We've preserved historical charms (hardwood floors, historical trim, retro fixtures) while adding in modern amenities (washer/dryer, dishwasher, stylish bathroom, new kitchen, electric car charger, etc!). Less than a mile from the Newburgh-Beacon Ferry launch, which connects you to Metro North Train. Note: Located on the second floor!

WalkabilityPetsBackyard

4.99 out of 5 average rating, 189 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

WalkabilityPetsAccuracy

5.0 out of 5 average rating, 105 reviews

Home in New Windsor

Farmhouse w/ Pool, Sauna & Hot Tub near Storm King

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!

PetsOutdoor spacesNearby

4.99 out of 5 average rating, 186 reviews

Chalet in Warwick

Mountain View Retreat w/ Hot Tub, Theater, and Gym

Thoughtfully designed, this secluded retreat is nestled on 12 acres of picturesque land in Warwick, NY. The exquisite home offers the perfect blend of luxury and tranquility, making it an ideal getaway for families and friends. Highlights include: -Huge deck with mountain views -115" 4k projection theater w/ seating for 10, wet bar, & popcorn machine -Hot tub w/ seating for 7 -Gym w/ indoor endless lap pool, Peloton bike, and yoga equipment -Game room w/ billiards & Pac-man -Gourmet kitchen

WalkabilityPetsCondition

4.97 out of 5 average rating, 153 reviews

A rustic log cabin is framed by tall trees, showcasing a spacious porch with a wooden railing. The front door features two circular glass panels, allowing natural light to enter the home. Lush greenery surrounds the property, enhancing its secluded appearance.

Cabin in Warwick

Magnificent Log Cabin Getaway with Private Lake

Enjoy the comforts of a magnificent log cabin set on six private acres in the Hudson Valley! Newly furnished, this 4-bedroom home comes with multiple living rooms, an indoor wood-burning stove, sauna, pool table, theater room, large private pond with dock, fire pit, and more! You'll be minutes away from restaurants, wineries, breweries, and activities for all members of your group. Near many trails, Greenwood Lake, and Mount Peter. Also a perfect getaway for skiing. Come escape and relax!

PetsOutdoor spacesHiking

4.98 out of 5 average rating, 129 reviews

Apartment in Stony Point

Gorgeous Suite w/ Private Entrance

Welcome to your private upstairs retreat with its own private entrance and bathroom. This charming efficiency offers a queen bed for restful nights, plus a loveseat sleeper sofa perfect for an adult or two small children. Enjoy the convenience of a mini fridge, coffee maker, and microwave. Step outside your door to our porch sitting area with a grill. Thoughtfully set up to feel both private and inviting, it’s a peaceful space to relax, recharge, and feel right at home during your stay.

Outdoor spacesPetsGrill

4.99 out of 5 average rating, 209 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.

Outdoor spacesWalkabilityAmenities

5.0 out of 5 average rating, 105 reviews

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

WalkabilityPetsGrill

4.93 out of 5 average rating, 102 reviews

Two wooden chairs are positioned on a gravel area, surrounded by vibrant yellow flowers. A stack of firewood is arranged nearby. In the background, a cabin with large windows is partially visible, framed by greenery.

Cabin in Warwick

[Rabbit Hill Cabin] Hiking/Private/Forest view

<Rabbit Hill Cabin> Take it easy at this unique and tranquil getaway in the woods. Gaze at the stars and enjoy the peacefulness of this fun , privately located little cabin. Warwick Permit #34238 Please feel free to inquire if you are traveling with more than 6 guests and book our neighboring listing . 🐕 Dogs permitted - $50 fee ⚡️level 2 EV Charger on premises . - Weber grill -Drip coffee maker and also a Kuerig

WalkabilityOutdoor spacesIndoor spaces

4.89 out of 5 average rating, 415 reviews

An inviting front porch features a comfortable bench and potted plants. The view captures a gravel path leading to a barn and lush greenery, with a gentle rain enhancing the tranquil atmosphere.

Farm stay in Goshen

Bright Farm House- Tranquil setting

Secluded 3-bedroom newly renovated late 1800 Farm house on a 50 acre working farm nestled in the Hudson Valley. Only 60 miles from NYC and close to everything the Hudson Valley has to offer. Many farms with seasonal apple picking and pumpkin picking ,West point , Woodbury Commons Premium outlets ,Resorts Casino. Tons of great local breweries ,Hudson Valley Wine Trail .. LegoLand Theme park is just 5 minutes away

WalkabilityOutdoor spacesHospitality

Popular amenities for Woodbury pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.94 out of 5 average rating, 137 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

PetsOutdoor spacesView

Home in Cornwall-on-Hudson

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, 190 reviews

Cozy Riverfront Victorian in the Hudson Valley

WalkabilityOutdoor spacesBathroom

4.92 out of 5 average rating, 167 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

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

Outdoor spacesTVCheckout

4.93 out of 5 average rating, 108 reviews

A private hot tub sits on a cement pad, surrounded by greenery and trees. In the background, lounge chairs are arranged in a clearing, adding to the serene outdoor setting.

Home in Newburgh

Charming Getaway 16mi to West Point!

WalkabilityOutdoor spacesCheck-in

4.97 out of 5 average rating, 112 reviews

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.

Home in Highland Falls

West Point Mountain House

Outdoor spacesWalkabilityBackyard

4.92 out of 5 average rating, 145 reviews

An aerial view captures a spacious lakefront property surrounded by lush greenery. Trees frame the yard, which gently slopes toward the water. The exterior of the house is clad in light gray, with multiple windows reflecting the natural surroundings. A patio area is visible near the water's edge.

Home in Putnam Valley

Crystal Wave LakeHouse

Outdoor spacesWalkabilityQuiet

4.96 out of 5 average rating, 141 reviews

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!

Outdoor spacesPetsTV

4.95 out of 5 average rating, 368 reviews

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!

Outdoor spacesPetsWifi

Pet-friendly home rentals with a pool

4.95 out of 5 average rating, 135 reviews

An aerial view captures a serene lake surrounded by lush, colorful foliage in autumn. The tranquil water reflects the sky and trees, while the distant mountains frame the scene, providing a sense of peace and natural beauty. Residential homes can be seen along the water's edge.

Cottage in Putnam Valley

Cozy Retreat w/ Pool, Cinema Room & Fire Pit

Outdoor spacesPetsCheck-in

4.96 out of 5 average rating, 104 reviews

A comfortable outdoor seating area features two armchairs and a coffee table, positioned near a vibrant blue pool. An umbrella offers shade, and the surrounding trees provide a serene backdrop, creating a relaxing atmosphere for outdoor gatherings.

Home in Florida

Legoland Mt Peter 3BR Pool Theater Hot Tub 1Pet

Outdoor spacesPetsView

4.99 out of 5 average rating, 103 reviews

Home in Redding

Retreat with Heated Pool, 1 Mile to NYC Train

Outdoor spacesPetsWifi

4.9 out of 5 average rating, 162 reviews

Home in Kerhonkson

Private Countryside Retreat with Pool & Hot Tub

PetsWalkabilityAmenities

4.88 out of 5 average rating, 218 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

WalkabilityOutdoor spacesDecor

4.9 out of 5 average rating, 534 reviews

An outdoor lounge area is framed by wooden beams, featuring dark seating arrangements around a small table. Soft lighting casts a warm glow over the scene, with landscaped greenery and vibrant flowers enhancing the ambiance. The resort-style pool is visible in the background, reflecting soft colors.

Apartment in Union

2 Bed Apt | Quick Access to NYC

PetsWalkabilityDecor

4.91 out of 5 average rating, 125 reviews

An aerial view showcases a charming farmhouse surrounded by lush greenery and the Catskill Mountains. A rectangular in-ground pool is visible in the backyard, bordered by a grassy area. A quiet country road runs alongside the property, contributing to the tranquil setting.

Home in Grahamsville

Spacious Catskills Farmhouse on over 5 acres!

Outdoor spacesPetsIndoor spaces

4.94 out of 5 average rating, 398 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

WalkabilityPetsSkiing

Private, pet-friendly home rentals

4.9 out of 5 average rating, 516 reviews

Chalet in Cold Spring

Mountain View Retreat

WalkabilityOutdoor spacesGetting around

4.97 out of 5 average rating, 245 reviews

A dining area features a long wooden table set for meals, with plates arranged on woven placemats. To one side, a bar area displays glassware and coffee equipment. Expansive windows frame scenic lake views, allowing natural light to brighten the space.

Cottage in Putnam Valley

Private Lake House 1 Hour to NYC & Near Westpoint

WalkabilityOutdoor spacesQuiet

Apartment in Fort Montgomery

A charming outdoor space features two light blue chairs positioned under a decorative pergola. A small barbecue grill is visible, surrounded by pots of various flowers and greenery. The area is bordered by mulch, with a small black table and chair set in the background.

4.84 out of 5 average rating, 117 reviews

1 Bed. apt, private entrance-close to West Point.

WalkabilityOutdoor spacesSleep quality

4.96 out of 5 average rating, 497 reviews

A charming log cabin is nestled among trees, featuring a stone patio with two green chairs. A wooden deck leads to a door, with a view of the lake in the background and a stone chimney adding character to the cabin exterior.

Cabin in Greenwood Lake

Cabinessence -on Greenwood Lake, NY #34370

PetsOutdoor spacesBeach

4.99 out of 5 average rating, 204 reviews

A serene view of Walton Lake captures a wooden dock extending into calm waters. The setting sun casts a warm glow over the landscape, reflected in the lake. Lush greenery frames the scene, enhancing the tranquil atmosphere.

Cottage in Monroe

Cozy Lake Cottage

WalkabilityPetsParking

Farm stay in Fort Montgomery

A charming house trailer is shown with white trim and multiple windows, surrounded by trees. An outdoor wooden deck features a grill, purple chairs, and a small pumpkin. Steps lead up to the entrance, offering access to the inviting outdoor space.

4.97 out of 5 average rating, 253 reviews

Secluded overlook cottage near West Point

WalkabilityOutdoor spacesTV

4.97 out of 5 average rating, 125 reviews

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

WalkabilityPetsAccuracy