Vacation rentals in Washingtonville

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Top-rated vacation rentals in Washingtonville

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

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Top guest favorite

A charming two-story cottage is surrounded by vibrant landscaping, featuring a mix of colorful flowers. The exterior is painted in green with maroon shutters adorning the windows. A wooden staircase leads to the upper entrance, while a welcoming front door is accented by a small planter.

Guest suite in Montgomery

Garden View Guest Cottage

Located under 15 min. to Stewart Airport...1 mile to City Winery , nearby Angry Orchards , 1/2 hour to West Point Charming cottage setting located in the village of Montgomery, NY, Come for the day or stay for a few to take in all this historic area has to offer. Walk to some of the best restaurants in Orange County or simply read a book in the gardens... Truly a great value since it's a true "apartment " like setting..not just a room, with all the conveniences and sleeps up to 4 people.

FamilyValuePets

4.94 out of 5 average rating, 586 reviews

Top guest favorite

The bedroom features a large bed with a white quilt, accented by decorative pillows in blue and yellow. A pink throw blanket is draped over a woven bench at the foot of the bed. Natural light fills the room through a window adorned with floral curtains.

Apartment in Woodbury

Maple Ridge Retreats - Apt B

Welcome to our stylish 1 bedroom apartment nestled in the serene woods of the beautiful Hudson Valley in New York. World-class shopping and restaurants are just a stone's throw away at Woodbury Commons, and we are conveniently located between the JW World Headquarters (25 minutes), Newburgh Assembly Hall (20 mins) and the new Patterson Visitor Center (50 mins). Guests planning a visit to Legoland (30 mins) or West Point Academy (9.4 miles, 25 mins) will find our location very convenient as well.

ValueLocationCondition

4.99 out of 5 average rating, 70 reviews

Superhost

An aerial view captures a sprawling landscape at sunset. Lush green trees frame open fields, while a river snakes through the background. The sky is filled with warm hues of orange and yellow, creating a tranquil atmosphere over the countryside.

Farm stay in Salisbury Mills

Rustic Ranch w/ Fire Pit, Trails & Grazing Horses

Escape the city and wake to the sound of grazing horses. Nestled on a 50-acre equestrian property, the Carriage House blends cozy charm with eclectic design and wide-open skies. Sip morning coffee with views of the Moodna Viaduct, then hike our private trails or explore Storm King Art Center. Unwind by the fire pit, or book a hands-on horse experience with our gentle herd. Nearby: wineries, hiking, farm markets,& MetroNorth (NYC in ~90 mins) Ideal for couples, small families, or solo retreat

FamilyValueComfort

4.86 out of 5 average rating, 110 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.

LocationValueTV

4.81 out of 5 average rating, 136 reviews

Superhost

A spacious living area features a comfortable gray sofa, accented by festive throw pillows. A light-colored coffee table sits in the center, surrounded by cozy armchairs. A large flat-screen TV is mounted on the wall, with natural light streaming through the nearby window.

Home in New Windsor

Farmhouse Getaway - 13mi to West Point

Gather with friends or family at our 1900s Hudson Valley farmhouse. This 3 bedroom unit offers one-level living with just one small step to the back deck—ideal for guests who prefer no interior stairs plus your own Hot Tub Bliss under the stars. Can accommodate large groups with 2 Kings, 1 Queen, plus 2 Queen sleeper sofas, twin daybed, twin trundle & floor mattress. Near Schunnemunk Mountain, Storm King, West Point and Newburgh waterfront. Fast Wi-fi, desks for remote work, free parking.

LocationValueLong stay

4.91 out of 5 average rating, 101 reviews

Guest favorite

A cozy living area is showcased with two accent chairs, one in a warm terracotta tone and another in vibrant red, featuring a playful design. The wooden floor complements the inviting atmosphere, while framed artwork adorns the walls, adding visual interest to the space.

Guest suite in Chester

Serene Victorian Guest Apartment with Clawfoot Tub

Escape to a stunningly renovated private 3rd-floor apartment in a 6000 sq ft. 1883 Victorian Manor in Blooming Grove, NY. Designed for 1–4 guests, this light-filled space offers comfort and classic charm in a peaceful country setting. Includes luxe beds, a clawfoot tub, French-door shower, and kitchenette with sunny breakfast nook. An ideal sanctuary. Views of wildflowers, quiet country, and cows next door. 3rd Floor up two staircases, rewarded with a stunning space and elevated views.

ValueLocationOutdoor spaces

4.94 out of 5 average rating, 412 reviews

Top guest favorite

Guest suite in New Windsor

The Loft Your Private Retreat

You'll be the only guests in this totally private second-floor space with your own exterior entrance and foyer. The Loft features a very large room with 12-foot ceiling, AC, heat. Two queen-sized beds, writing desk, bistro table, books, 42 inch TV - plenty of room to relax, work or simply unwind. Enjoy morning coffee/tea and morning muffins. Step through the sliding glass door onto your private east-facing balcony, a lovely spot to start the day. Private. Spacious. Comfortable. Peaceful.

ValueLocationAccess

4.97 out of 5 average rating, 314 reviews

Top guest favorite

Guest suite in New Windsor

A Cozy-Luxe Getaway | Scenic & Serene

The Nook is a thoughtfully designed upstate retreat, tucked in the heart of the Hudson Valley. It combines elevated design and natural simplicity: with tall ceilings, warm textures, and views of the distant mountains. The Nook is an intimate escape designed for rest, connection, and inspiration — the perfect getaway from the everyday hustle. It’s only 90-minutes from NYC and a short drive from the Hudson Valley’s best waterfronts, trails, wineries and dining experiences.

LocationFamilyDecor

4.93 out of 5 average rating, 42 reviews

Guest favorite

A modern kitchen area is presented with open wooden shelves displaying dishes, glassware, and decorative items. Below, a gas stove and black refrigerator are complemented by a light fixture and a collection of utensils, offering a functional and organized space.

Cottage in Goshen

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Picture this... You escape to a relaxing, picturesque, and peaceful country cottage and enjoy some of your favorite convenience amenities like 1 Gig Wifi and your favorite streaming sources. Just 10 minutes to LEGOLAND, 3 miles to the famous Orange Heritage Trail, and less than 20 minutes to America's oldest winery, Brotherhood, this cottage has something to offer for everyone. You'll be minutes from conveniences like Target but taking in the views, you'd never know it.

FamilyValueAmenities

4.92 out of 5 average rating, 386 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

Charming, historic 1910 home in Cornwall, NY with breathtaking sunsets, large yard, large living room, patio for BBQ's and outside firepit (when allowed to burn by local authorities). Our home is perfect for a weekend away or vacation with family and friends. Located a short 1-hour drive from New York City and a short distance to many hiking trails and the Hudson River. We love dogs! There are many dog-friendly hikes and a large dog park nearby.

LocationValueAccuracy

4.98 out of 5 average rating, 59 reviews

Guest favorite

Barn in Mountainville

Renovated Red 1890’s Hudson Valley Barn

Renovated barn in Mountainville, NY at the base of the Schunnemunk hiking trails. 1 mile from Storm King Art Center. 3 miles to Cornwall. 10 minutes from Woodbury Common Premium Outlet. 15 minutes to West Point. Private stairs & balcony leads to 500 square foot second-story space. You get the entire upstairs to yourself. The NYS Thruway does run between the house and the mountain. There is highway noise. TV has a ROKU. Strong WIFI.

ValueLocationWalkability

4.95 out of 5 average rating, 168 reviews

Top guest favorite

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

FamilyValueKitchen

4.89 out of 5 average rating, 421 reviews