Holiday houses in Shenandoah

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Top-rated holiday 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

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.

FamilyValueHeating

4.81 out of 5 average rating, 136 reviews

Top Guest favourite

Apartment in Holmes

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.

LocationFamilyBackyard

5.0 out of 5 average rating, 150 reviews

Guest favourite

Home in Hopewell Junction

Hudson Valley Gateway, Near Beacon 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 Pool closed SEPT 15 2026

LocationValueHospitality

4.83 out of 5 average rating, 47 reviews

Top Guest favourite

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!

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

LocationFamilyCleanliness

4.99 out of 5 average rating, 105 reviews

Top Guest favourite

The outdoor area features a grassy lawn surrounded by trees, with a rustic wooden table and chairs set for gathering. A stone pathway leads through the yard, where small trees and decorative birdhouses add charm to the tranquil natural setting.

Cabin in Carmel Hamlet

Peaceful Forest Cabin

Nestled down a quiet dirt road, this authentic, rustic 1800s log cabin has been lovingly updated with timeless style and all-new appliances in 2023. Perfectly situated on 4 private acres with native and perennial pollinator meadows! Lower Hudson Valley and surrounded by over 1,000 acres of State Forest, it's easy to stay in and bathe in nature, read a book, and bird-watch. Or, there’s easy access to hiking, shopping, and dining in nearby Katonah, Cold Spring, Beacon, Hudson, or NYC!

FamilyLocationKitchen

4.94 out of 5 average rating, 112 reviews

Top Guest favourite

A peaceful outdoor view showcases a well-maintained yard with lush green grass and various trees. A pathway made of stones leads to the entrance of the building, which features a covered porch under a metal roof. Sunlight filters through the surrounding foliage.

Guesthouse in Fishkill Village

Hudson Valley Studio in the Village of Fishkill NY

This spacious studio is in a quiet cul-de-sac and under a half mile walk from the Village of historic Fishkill, NY. Also, only a 10 minute drive to Beacon, NY! It is a private dwelling that includes a full kitchen, 1 new Queen bed, 1 new pull out bed, and a separate room for laundry. Plenty of drawers and closet place caters to up to 4 guests for whichever Hudson Valley activity you're in town for. Come enjoy the atmosphere of this Hudson Valley studio!

ValueFamilyComfort

4.91 out of 5 average rating, 146 reviews

Guest favourite

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

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.

FamilyLocationAir conditioning

4.96 out of 5 average rating, 179 reviews

Guest favourite

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

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!

LocationValueAccess

4.89 out of 5 average rating, 106 reviews

Guest favourite

Tiny home in Hopewell Junction

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!

LocationValueOutdoor spaces

4.95 out of 5 average rating, 583 reviews

Top Guest favourite

Home in Redding

Retreat with Heated Pool, 1 Mile to NYC Train

The pool is open for the 2026 season. Escape to a stunning 4-BR home on 2 acres in Redding, CT (#1 Small Town). Just 90 mins from NYC, this luxurious retreat comfortably fits 8 guests. Enjoy hotel-style amenities, a heated saltwater pool, and a gourmet kitchen. Breathe in fresh country air in a peaceful, park-like setting. Perfect for families, offering a blend of modern comfort and outdoor living.

FamilyValueDecor

4.99 out of 5 average rating, 109 reviews

Guest favourite

A winter scene is visible through a window, showcasing a snow-covered landscape. Green shrubs peek through the snow, and tall trees are blanketed in white. Soft yellow lights from nearby decorations create a warm glow against the chilly blue tones of the evening sky.

Home in Wappingers Falls

Ideal for students and those who travel for work.

It is essentially a furnish one bedroom apt with its own bath and kitchen and its own entrance. We will accommodate the guest depending on their privacy and needs within limits. Our cozy living room features a versatile L-shaped layout with two single daybeds. It serves as a comfortable sectional lounge by day and provides two separate sleeping spaces at night.

ValueLocationCheck-in

4.79 out of 5 average rating, 135 reviews

Guest favourite

The living area is arranged with a comfortable sofa and armchair positioned facing a flat-screen television mounted on the wall. A light-colored area rug covers the hardwood floor, while a wooden side table adds functionality to the space.

Apartment in Fishkill Village

Private, spacious apartment

Relax at our peaceful and centrally-located home. Private one bedroom walk-out apartment with full kitchen. Only minutes away from Main Street Fishkill and Beacon. Sleeps 4 comfortably with a full size bed in the private bedroom and a queen size pull out couch in the living space.

FamilyValueAccess

4.88 out of 5 average rating, 57 reviews