Holiday rentals in Maybrook

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Top-rated holiday rentals in Maybrook

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

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Top guest favourite

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.

LocationValueIndoor spaces

4.94 out of 5 average rating, 582 reviews

Top guest favourite

A spacious living area features large glass doors that bring in natural light and provide views of the outdoors. Comfortable seating includes a modern sofa and armchair, accompanied by a coffee table and a dining area positioned nearby.

Chalet in Pine Bush

Spacious A-Frame Getaway near Hiking and Wineries

Escape to our A-frame in the heart of the Shawangunks, nestled within the picturesque Hudson Valley. Just 1.5-2 hours from NYC, our spacious and serene home is perfect for a peaceful retreat, outdoor adventures, and exploring local wineries. Nearby attractions include Lake Minnewaska Park, Mohonk Preserve, Sam’s Point, the Shawangunk Wine Trail, Ellenville and Blue Cliff Monastery. The location also provides convenient access to explore many of the Hudson Valley and Catskill towns and villages.

FamilyValueAccuracy

4.97 out of 5 average rating, 142 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.

ValueFamilyGrill

4.81 out of 5 average rating, 136 reviews

Guest favourite

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

FamilyValueBiking

4.87 out of 5 average rating, 109 reviews

Guest favourite

A serene outdoor space features a private pool surrounded by a well-maintained garden. A koi pond with lily pads adds tranquility, while lounge chairs provide comfortable seating. Lush greenery and colorful shrubs create a peaceful atmosphere, perfect for relaxation and enjoying nature.

Home in Montgomery

Serene Hudson Valley Escape Hottub/Pool/King Suite

Welcome to our comfortable haven, perfectly situated to offer the best of the Hudson Valley! This centrally-located gem ensures closeness to the attractions the area has to offer. Explore Legoland, Angry Orchard, fine dining & shopping in historic Downtown. Nature enthusiasts will love hiking the nearby mountain ranges. Central to WT Farms & tours. See the MET & NYC offerings with the Beacon train. Enjoy the perfect blend of relaxation, adventure, & convenience. We look forward to hosting you!

LocationFamilyComfort

4.92 out of 5 average rating, 51 reviews

Top guest favourite

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!

LocationValueIndoor spaces

5.0 out of 5 average rating, 105 reviews

Guest favourite

Home in Montgomery

Treehouse-Inspired Cabin Escape w/ Theatre & Gym

Welcome to your getaway in Montgomery, where cozy cabin charm meets modern comfort. This 3-bedroom, 3.5-bath home offers a treehouse vibe surrounded by nature. Enjoy a private pool, theatre room, game room, gym and fireplace. Spacious living areas and a full kitchen make it perfect for groups or families. Relax, recharge, and make unforgettable memories in this peaceful yet conveniently located getaway. We're also conveniently located 20 minutes away from hiking trails and skiing mountains!

ValueFamilyHospitality

4.75 out of 5 average rating, 8 reviews

Top guest favourite

The cottage is surrounded by lush green grass and mature trees, offering a serene outdoor setting. A well-maintained pathway leads to the inviting entrance, while the structure features light-colored siding and large windows, creating a seamless connection with nature.

Cottage in Goshen

Cheery & Peaceful Farm Cottage, 10 Min to LEGOLAND

When you're looking to get away from it all and experience some peace and quiet surrounded in nature, this Cottage fits the bill. Whether it's enjoying fireflies over the field at dusk or enjoying cheerful birds in the morning, this beautiful Cottage sets the stage for you to be refreshed and renewed by the time you check out. While it feels like a secluded oasis, this place is also 10 minutes from LEGOLAND, Target, and all your other favorite conveniences. We look forward to hosting you.

LocationFamilyWalkability

4.92 out of 5 average rating, 346 reviews

Guest favourite

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 1–6 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.

ValueFamilyParking

4.94 out of 5 average rating, 405 reviews

Top guest favourite

Home in Montgomery

The B House

The “B” house, constructed in the 19th century, underwent renovations and modernizations to accommodate contemporary living standards while preserving its original architectural charm. The house boasts magnificent beams that span the entire interior, creating a sense of grandeur. Additionally, newly renovated appliances and updated bathrooms have been installed throughout the property. The kitchen features an expansive open space, elegant countertops, cooking essentials are top-notch.

FamilyLocationNearby

4.82 out of 5 average rating, 22 reviews

Guest favourite

A modern dining area features a wooden table surrounded by stylish chairs. Five pendant lights hang above the table, providing soft illumination. A plant stands nearby, contributing to the fresh ambiance, while a sliding door offers access to outdoor space.

Cottage in Pine Bush

Modern 3BR BoHo Retreat/Nearby Hiking, Wineries

Our newly modern bohemian cottage (aka Green House!) is perfect for your next weekend getaway or a new WFH locale. Decompress from city stress in this calm, serenely appointed private home. Close to attractions but far enough away to escape, you'll never want to leave. NYC: 79 mi. Hunter Mountain Ski Resort: 60 mi. Pine Bush - groceries/supplies: 7 mi. Middletown - shopping (Walmart, Target, Best Buy, Home Depot): 16 mi. Hiking trails: 7 mi. Horseback riding: 7 mi. Sky diving: 15 mi.

ValueFamilyOutdoor spaces

4.93 out of 5 average rating, 133 reviews

Top guest favourite

A striking red barn-style building is framed by lush greenery and a well-maintained stone wall. The entrance features double garage doors, complementing the rustic charm. Soft ornamental grasses and flowering plants add a touch of color to the exterior.

Barn in Montgomery

16taft

16taft is a newly built loft set in the quaint Village of Mongomery in the Hudson Valley. The upper level of a barn-style building, it is located on a quiet street walking distance to cafes, restaurants and shops. With a 1,000 sf open floor plan including vaulted ceilings with exposed beams, barn lights and wide board pine flooring it has old charm for a new building. Outdoors, an impressive sunken circular fieldstone patio with BREEO fire pit is available for your enjoyment.

LocationFamilyAccuracy

4.98 out of 5 average rating, 44 reviews