Holiday houses in Shenandoah

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Top-rated holiday rentals in Shenandoah

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Guest favourite
A dining area is shown with a round wooden table at the center, adorned with a vase of flowers. Large glass windows frame a serene lakeside view, with blooming flowers in the foreground and lush greenery. Soft sunlight reflects off the water, creating a tranquil atmosphere.
Home in Carmel Hamlet
4.92 out of 5 average rating, 208 reviews

Lux Bungalow on the Lake

Beautiful, light flooded, waterfront home 1 hour from New York City. The 2 bedroom home is on picturesque Lake Carmel. Wake up, eat, sleep and relax to the tranquil view of the glistening water - truly an oasis! Take in a sunset while eating a meal at home, explore the shops and restaurants in a cute nearby town, take a walk around the lake, read a book by the cozy fireplace, hike, cook, kayak, ski, or just sit and enjoy. Centrally located close to Hudson Valley, Westchester and Connecticut.

Guest favourite
A historic farmhouse is set among vibrant greenery and blooming orange flowers. The expansive front porch features classic white railings and is lined with hanging planters. The structure is nestled between two large trees, providing a serene backdrop against the clear blue sky.
Guest suite in Dover Plains
4.91 out of 5 average rating, 344 reviews

Hoppy Hill Farm House

Enjoy the simple country life in this historic farmhouse. Watch the sun rise over the breathtaking mountain views from the front porch while sipping a cup of coffee/tea. For the more adventurous, there are lots of Appalachian Trail hiking opportunities, and nature preserves to enjoy. Plenty of quaint towns near-by: Kent, Millbrook, Amenia, Wassaic for great food, coffee shops, antiques, parks, breweries and vineries. Inside, you will feel right at home in this comfortable one bedroom apartment.

Top Guest favourite
A spacious studio apartment features large windows allowing natural light to fill the room. A comfortable king size bed is positioned alongside a cozy seating area with a sofa and coffee table. A textured area rug covers the hardwood floor, adding warmth to the space.
Apartment in Pawling
5 out of 5 average rating, 116 reviews

Quiet Studio Apartment in Pawling

For getaways or visiting the area, this peaceful sanctuary awaits your arrival in Pawling. A fresh clean studio apartment with idyllic views of the forest, stone walls, and distant mountains. Awake to the sound of birds and beautiful sites. With a king size bed, kitchenette, desk, Smart TV, WIFI, full bath with walk-in shower. Big sliding glass door to private deck overlooking native landscaping. 1 mile to village for restaurants, bakeries, & night spots. 7 min by taxi to Darryl's House Club.

Top Guest favourite
The exterior of the modern chalet is surrounded by lush greenery, showcasing a spacious sun room with large windows. A hammock is visible between trees, inviting relaxation. The property features a gently sloping yard leading down to the tranquil lakefront.
Chalet in Carmel Hamlet
4.97 out of 5 average rating, 115 reviews

Secluded Lakefront Chalet•Firepit•Yard Dogfriendly

Just over an hour from NYC, this secluded, dog-friendly lakefront chalet offers 200’ of private shoreline, fenced yard and sunroom with serene lake views. Thoughtfully styled with collected pieces from my travels, it blends quiet luxury with modern comfort. Cozy up by the fireplace, enjoy vinyl or a movie, watch snowfall, spot wildlife, explore nearby trails, unwind by the fire pit and rest in the king-size bed. Romantic, peaceful, beautifully secluded – your perfect winter lake escape awaits.

Top Guest favourite
A charming cabin is nestled among vibrant trees displaying autumn foliage. A wooden staircase leads to the entrance, flanked by natural stone walls. Outdoor seating arrangements are visible on the deck, offering a peaceful retreat in a wooded setting.
Cabin in Fishkill
4.96 out of 5 average rating, 126 reviews

Secluded Hilltop Cabin near Beacon & Cold Spring

3 private acres atop small mountain. Feels like you're way upstate - check out the reviews! Hi-speed WiFi. Next to forest preserve and hiking trails. Furnished deck w grill overlooks Mt. Beacon sunsets. Loft w/queen and twin mattresses + pull out couch & twin-size mattress day bed on the porch. Perfect for 2, comfortable for 3, but 4 is probably max comfort since it's a small space. Please note that the road heading up there is steep. A car with AWD is ideal but a sedan will make it up too!

Top Guest favourite
A bright sleeping area features a spacious bed with white linens, complemented by two decorative pillows. A small side table with a lamp is positioned beside the bed. Light wood flooring and a window with dark curtains add warmth to the space. A chair and artwork are visible along the wall.
Apartment in Beacon
4.93 out of 5 average rating, 147 reviews

Cozy, Small Studio with Backyard & great A/C

Cozy, small studio on quiet block. Near Main Street, Roundhouse, hiking, restaurants. Fully private space & entrance, shared backyard, new A/C, wifi. Walk everywhere. Queen-sized bed. BEFORE YOU BOOK - 200 year old house - hosts live upstairs and there is another guest apartment. You WILL NOTICE sounds from others. QUIET HOURS from 10 PM to 8 AM. As a courtesy to others, please keep conversations quiet after 10 PM. We only book guests with favorable Airbnb reviews. NO SMOKING please.

Top Guest favourite
A cozy room with a small kitchenette and a dining area featuring a round table and two chairs. Natural light fills the space through a glass door, which leads to the side yard. A minimalist wall art piece adds a touch of character to the room.
Guest suite in Beacon
4.97 out of 5 average rating, 333 reviews

Hiker's nest

This is a cozy room with private forest views and all the basic amenities (small kitchenette). We are located next to the entrance of Mount Beacon park (the free Loop Bus from the station drops you on our corner), a three-minute walk to the trail entrance, and a 25 minute walk to the train station and Main Street. The room is attached to the main house, but you have your own entrance with code access. We live in the main house, so we are here to answer questions or help with your stay.

Top Guest favourite
A rustic bench is positioned along a wooden fence, offering a vantage point of rolling hills adorned with autumn foliage. The scene captures a bright, open sky dotted with fluffy clouds, enhancing the natural beauty of the surrounding landscape.
Apartment in Marlboro Township
4.98 out of 5 average rating, 421 reviews

Cliff Top at Turtle Rock

Cliff Top retreat with a one hundred mile view of the Shawangunk's and the Catskill Mountains, surrounded by thousands of acres of ancient forest. Conveniently located in the Hudson Valley Wine and Orchard country. Twenty minutes from Beacon and New Paltz. Furnished with mid-century and 18th century period furniture and art work, yet with all the modern conveniences. Uber and Lift an easy five minutes away. The ancient forest contains many Stone Age rock shelters and calendar sites.

Top Guest favourite
Apartment in Newburgh
4.88 out of 5 average rating, 230 reviews

Special Nest w Private Entrance River View Porches

Front and back porch, river views, spacious living areas, new & fresh kitchen, and *two* bathrooms make this apartment the ultimate landing spot for a fun vaycay! Located on a street filled with intricate historical homes, this first floor apartment offers an accessible and comfortable getaway. A large backyard is shared with other guests, and sweeping river views are only steps away from your front door. Private entrance, plus easy parking and an electric car charger if you need it!

Top Guest favourite
A spacious bedroom features a large black bed with gray bedding, complemented by a decorative pillow. Nearby, a simple black bench and a floor lamp provide additional functionality. Natural light enters through a window covered with light curtains, and a leafy plant adds a touch of greenery.
Apartment in Beacon
4.91 out of 5 average rating, 111 reviews

Beacon Hills Retreat Apartment

Welcome to Beacon Hills Retreat! This upstairs apartment, in a rustic home, set just outside bustling Beacon, NY. A 7 minute drive along Fishkill Creek brings you downtown, with art galleries, fabulous restaurants, hiking, and nightlife. Settle down in this cozy apartment tucked into the side of Mount Beacon. Explore the wooded areas, interact with nature and just relax. The lovely shaded private deck is the perfect place to unwind. Breathe in the mountain air. You've arrived.

Top Guest favourite
A sunlit open space features a light-colored wooden floor and white walls. Two large windows invite natural light, while a patterned area rug adds warmth. A small table and chairs are arranged nearby, creating a versatile area for dining or work.
Guesthouse in Cold Spring
4.99 out of 5 average rating, 199 reviews

Modern+bright forest escape - near village & train

Modern, efficient, and elegant private flexible garden apt. Guesthouse can be used as a studio apartment, or as a private personal retreat space for art/work/rest/meditation. Hiking trails available right out the door, and just a few minutes walk to Cold Spring's vibrant Main Street and Metro North train station to NYC and beyond. Comfortable bed, all modern amenities. Private patio. Native pollinator gardens and forest surround. Solar orientation brings in natural light.

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
4.9 out of 5 average rating, 114 reviews

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!

Popular amenities for Shenandoah holiday rentals

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