Vacation rentals in Shenandoah

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Top-rated vacation rentals in Shenandoah

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

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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

4.81 out of 5 average rating, 134 reviews

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.

Top guest favorite

Apartment in Holmes

5.0 out of 5 average rating, 142 reviews

Top Side

Welcome to Top Side! Nestled in Holmes, NY, Top Side offers lovely views of Whaley Lake. Whether you're looking for a relaxing getaway or an adventure, you'll find plenty of reasons to fall in love with this spacious apartment which is designed to help you unwind and recharge. The Hudson Valley is brimming with activities and attractions for everyone. From historic landmarks and charming villages to outdoor adventures and local dining, you're never far from something special to experience.

Guest favorite

The exterior view of a multi-level home features a light blue façade with white trim. A wide staircase leads to the main entrance, flanked by neatly landscaped lawns and shrubbery. A lamp post adds subtle lighting, while the surrounding trees provide a natural backdrop.

Home in Fishkill Village

4.89 out of 5 average rating, 38 reviews

Immaculate Home W/ Pristine View

Spectacular views less than a 90-min scenic drive to NYC. 5 mins from shopping, restaurants, highways, parks, & trails. This stunning home is gorgeous w/ a modern kitchen, pristine furniture, formal dining rm, large backyard & patio, parking for 4+ cars & three different sections of the home- perfect for quiet time away from the crowd. Made available for the first time to the public-don't miss this opportunity to stay at the home foreign dignitaries & celebrities choose over NYC hotels.

Superhost

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

5.0 out of 5 average rating, 101 reviews

Home in Cold Spring- Farm Stay!

Escape to our charming home nestled on five acres of farmland. This stay offers both seclusion and convenience, providing an ideal retreat for families, friends, or anyone seeking a peaceful countryside experience. Outdoor Space: -Walkable property featuring goats, chickens, horses, and donkeys -Large front porch featuring stunning mountain views and sunsets -Nearby hiking trails Location: -Five-minute drive to the quaint village of Cold Spring -Many shops, restaurants, and river views

Guest favorite

Home in Hopewell Junction

4.91 out of 5 average rating, 45 reviews

Relax, enjoy nature and a pool just 1 hr from NYC

Unwind with your loved ones at this serene getaway. This charming home boasts 4 bedrooms (1 king bed, 2 queen beds, 2 bunk bed each with a full bed and a twin bed, 1 twin bed) and 3 bathrooms with lovely backyard, pool, game room and plenty of nearby activities like horseback riding, water park, playground, restaurants and more. Enjoy the privacy this home offers. Near Taconic Parkway and route 684. Pet fee $100.00 Smoking cigarettes, vaping or hookah $350.00 FEE

Guest favorite

An open living space features high cathedral ceilings and warm wood flooring. A sleek sectional sofa is positioned around a glass coffee table. A staircase with wooden railings leads to an upper level, while a cozy fireplace is situated next to a television mounted on the brick wall.

Home in Mahopac

4.96 out of 5 average rating, 176 reviews

Peaceful & Spacious Retreat

Big and beautiful house fully renovated in 2020 sitting on half an acre of land in Mahopac. Open floor concept with high cathedral ceilings in living space. Kitchen fully stocked with everything you need to cook and bake. Oversized bedrooms and two bathrooms. Great for a weekend getaway (about 1hr drive from NYC). EV friendly - Tesla universal charger located at property to charger your Tesla or EV vehicle (integrated J1772 adapter) during your stay.

Guest favorite

An outdoor seating area is showcased, featuring a covered patio with comfortable furniture arranged for relaxation. The surrounding landscape includes manicured shrubs and a gravel pathway that leads to an expansive green lawn. Trees line the background, offering a serene natural setting.

Home in Wappingers Falls

4.9 out of 5 average rating, 102 reviews

La Casita - Home Away From Home.

✨ Discover Serenity at La Casita 🏠 — Your Hudson Valley Escape ✨ Cozy 3-bedroom, 1.5-bath retreat near Dutchess, Marist 🦊 University, Vassar, and the Culinary Institute of America 🧑‍🍳, it’s ideal for visits or getaways. Enjoy nearby wineries 🍷, orchards 🍎, farm markets, and hiking trails 🥾, or simply unwind and soak in the beauty of Hudson Valley’s seasons 🌻☀️🍁⛄️. Need anything specific? We’re happy to help make your stay perfect!

Superhost

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

4.95 out of 5 average rating, 368 reviews

Hilltop Hideaway Forest Villa on 13 acres!

Our artistic, spacious , comfortable home is set on 13 (fairytale-esque) private, forest acres. We are minutes away from hiking trails, swimming lakes, and the Hudson River where you can kayak. The house is located on 13 acres of land just minutes away from the vibrant shopping of downtown Cold Spring, NY. It is surrounded by lakes and hiking trails, including the Appalachian Trail. We are minutes away from the Cold Spring train station.

Guest favorite

A living area features large windows that allow natural light to fill the space, offering views of the surrounding woods. Two light-colored sofas with decorative pillows are arranged around a glass coffee table, positioned on a textured area rug.

Home in Carmel Hamlet

4.85 out of 5 average rating, 34 reviews

Hudson Valley Cabin in the Woods

Forget your worries in this spacious and serene space. Located on 8 acres in the woods, this house has everything. Beds for 10 people, fireplaces, a Jacuzzi, and a private pond. This house is 20 minutes to Beacon, Cold Springs, and Patterson Ski Resort. There are dozens of local farms, hiking trials, galleries, and apple orchards to visit during your stay. Perfect for family vacations, trips with friends, and NYC getaway weekends.

Guest favorite

Tiny home in Hopewell Junction

4.95 out of 5 average rating, 581 reviews

The GlassHouse: Hudson Valley Tiny Home w/Firepit

The GlassHouse is the much talked-about experience that we had crafted within a sprawling forest preserve. Its wrap-around windows allow breathtaking views to bring out the romantic in all of us! We are stone’s throw up against the Appalachian Trail right on the Dutchess/Putnam line and are less than an hour from Manhattan. Minutes from Fahnestock & Hudson Highlands State Parks & the Empire State Trail!

Superhost

An open-concept great room features floor-to-ceiling windows offering unobstructed views of the lake. Exposed wooden beams accentuate the ceiling, while a spacious dining table and comfortable seating area create a welcoming space. Natural light is complemented by modern pendant lighting throughout.

Cabin in Holmes

4.87 out of 5 average rating, 133 reviews

Charming Hudson Valley Lakefront Escape with Views

A year-round waterfront home with gorgeous unobstructed views of Whaley lake provides the perfect escape for a long weekend or vacation. Enjoy swimming and lake activities via private direct lake access. Spacious boathouse deck for entertaining or sunbathing. Cozy up to a two-story stone fireplace while enjoying the fall and winter colors. Just 10 minutes from Thunder Ridge Ski area.

Guest favorite

A spacious and inviting pool area features a large, unheated swimming pool surrounded by a stone deck. Sun loungers are positioned near the water, and lush greenery provides a natural backdrop, creating a serene outdoor environment.

Guest suite in Holmes

4.97 out of 5 average rating, 224 reviews

Huge eclectic space w/ private pool. 1.5hr to city

1.5 hrs from NYC; minutes driving from hiking trails; 20 min from Beacon and Cold Spring! The bottom floor of this 1865 Carriage House has been transformed into an eclectic retreat. The 2500 sq ft private apartment has a room for every mood and super unique decor in every corner! There is also a vintage/antique shop on the property— 20% off for our guests ;)