Vacation rentals in Castleton-on-Hudson

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Top-rated vacation rentals in Castleton-on-Hudson

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Guest favorite

A newly constructed wooden deck features two white Adirondack chairs positioned on its surface. Soft lighting is installed along the railing, creating a warm ambiance. The background showcases trees silhouettes against a twilight sky.

Apartment in Rensselaer

4.93 out of 5 average rating, 41 reviews

ThE NooK

Kick back and relax in this quiet, calm, stylish space. Enjoy our little place with a new deck and a big backyard over looking 6 acres of woods and a small creek. You can only see the creek in late fall and throughout winter. We are extremely clean and cherish our place so please treat it good 😊. It’s very well kept and orderly. We offer 2 parking spaces. There are plenty of nearby activities to enjoy during your stay such as a drive in theater, ice cream shops, shopping centers, etc. Book now!

Top guest favorite

The welcoming house, set on a lush green lawn, features a charming front porch with a dark blue door. Flanking the entrance are neatly trimmed shrubs and trees, enhancing the inviting curb appeal. The surrounding landscape offers a serene outdoor space with well-maintained grass.

Home in Rensselaer

4.98 out of 5 average rating, 167 reviews

3bdrm Cozy Cape w/ Fireplace & close to Cap Dist.

The house is close to so many things to do in the area: shopping, skiing, biking, min's from RPI, UAlbany, HVCC, and just 40 min to Jiminy Peak. After your day out you will enjoy coming back to grill dinner and enjoy a drink on the deck. Fun and relaxation for everyone. The property includes a master suite w/ full bathroom and laundry on the 1st floor and 2 bedrooms with a full bathroom upstairs. There is also a full kitchen and dining room on the first floor for making and enjoying meals.

Guest favorite

A cozy living area is highlighted by natural wood paneling and large windows allowing ample sunlight. A comfortable gray couch is positioned near a warm lamp, while a decorative basket and a small table with a subtle blue rug complete the inviting atmosphere.

Barn in Stuyvesant

4.9 out of 5 average rating, 20 reviews

Copper Top Mini Barn

Visit Columbia County NY for a refreshing getaway in our brand new, freshly renovated Mini Barn that sits on over 30 private acres. Enjoy the morning light, sunsets, moonlight, and star gazing over open fields. Walk the trails to beautiful views of the Catskills Mountains, listen to the singing birds or take a short drive to the best towns and villages in the Hudson Valley. You will leave The Copper Top Mini Barn feeling relaxed and recharged. Perfect for a fall getaway or a summer retreat.

Guest favorite

A spacious living area is adorned with a large area rug and a comfortable blue bed. Large windows allow natural light to illuminate the room, highlighting the warm yellow walls and the vintage chandelier. A small coffee table and plush seating invite relaxation.

Condo in Center Square

4.9 out of 5 average rating, 287 reviews

Elegant, spacious studio apt in historic mansion

Welcome to the Plaza Suite, a newly renovated studio condo in an historic Center Square mansion. Enter through a grand reception hall/art gallery and climb the oak staircase to the sunny and spacious second floor apartment. There's a nice view of State Street and the Empire State Plaza. Features include: a new fully equipped kitchen, comfy lounge area, dining /work table, renovated vintage bathroom, walk-in closet and new queen bed. Feel free to enjoy a glass of wine in the art gallery.

Top guest favorite

Cottage in Nassau

4.96 out of 5 average rating, 28 reviews

Lakeview Oasis- sunset view, boat cruise, kayak

Relax and refresh at Casa Miranda’s retreat,surrounded by calm waters and resort-like serenity. This breathtaking waterfront home offers the perfect blend of luxury and nature. The private dock beckons water enthusiasts, providing direct access to the shimmering waters for boating, fishing, or simply basking in the calm ambiance. Perfect for romantic getaways, family fun, groups or solo relaxation. This secluded retreat offers comfort, charm, and nature’s beauty all in one serene setting.

Top guest favorite

A spacious bedroom features a large queen bed with a white duvet and decorative pillows. Two sets of French doors open to an outdoor view, flanked by soft curtains. A cozy seating area with a light-colored sofa adds comfort, illuminated by natural light from the windows.

Guest suite in Valatie

4.98 out of 5 average rating, 255 reviews

Guest Suite in Old Chatham Hunt Country

Looking for all the perks of a hotel while staying at a house in the country? This tranquil, light filled room overlooks horse pastures and a dirt road in the heart of Old Chatham hunt country. A private entrance leads to a guest suite which includes a queen size bed, sitting area, kitchenette, and walk-in closet. Located on the first floor of a newly built, net-zero home. Power comes from solar and solar water panels provide for guilt-free hot showers! 50 MBPS fiber optic Internet!

Guest favorite

The entrance to a Hobbit house is framed by lush greenery and natural stone. A curved, grassy roof merges with the surrounding trees, while a stone pathway leads to the large wooden door. Decorative lanterns are positioned above the entrance, enhancing the rustic charm.

Earthen home in West Sand Lake

4.97 out of 5 average rating, 207 reviews

The Hobbit House at June Farms

Enjoy 120-acres of beautiful farmland while you stay in your very own Hobbit house! Nestled in the hills of Hudson Valley, June Farms is a gorgeous animal sanctuary. During your stay, you will be able to meet our Shire horses, Scottish highland cows, Gloucestershire spotted pigs, Nigerian dwarf goats, many chickens and ducks! From June 1 - Labor Day, the bar & restaurant is open most days for you to enjoy (check our calendar to be sure). We look forward to meeting you!

Guest favorite

An inviting living space features a handcrafted wooden bed against a stone accent wall. A round wooden dining table is accompanied by two chairs. Comfortable seating is provided by a black leather sofa. Unique patterned stone flooring adds character to the room.

Farm stay in Coeymans Hollow

4.86 out of 5 average rating, 670 reviews

Magic Forest Farm's Mountain View Suite

Our 225 acre farm is predominantly forested, with miles of hiking trails and incredible views. Nestled in the foothills of the Catskills near Albany, we are the last home on a dead end road and have multiple secluded rentals. We are a homestead devoted to the principles of organic farming and self reliance. We grow much of our own food and forge many types of wild mushrooms. You will be sure to enjoy friendly animals around the farm and a private fenced Koi pond.

Guest favorite

A peaceful front deck features two black chairs and a glass table, offering a view of the green landscape and Hudson River. The sun shines brightly in the background, illuminating the surroundings and creating a serene outdoor space.

Cottage in Stuyvesant

4.94 out of 5 average rating, 166 reviews

Perfect Cottage On A Hill With A View

A peaceful cottage with views of the Hudson River and Sunsets over the Catskill Mountain Range. Personal, private and all inclusive this little cottage is an incredible place to unwind relax and soak in the beauty of the Hudson Valley. With easy access many local hikes, swimming holes, towns and shopping you’ll find This little cottage to be the perfect place to relax with nature & indulge in all of the luxuries that the Hudson Valley has to offer.

Guest favorite

A grassy area is presented with two black metal benches positioned on either side of a small garden. Lush trees and vibrant greenery surround a historic colonial-style mansion, which is visible in the background against a clear sky.

Apartment in Troy

4.89 out of 5 average rating, 35 reviews

Charming Hudson riverfront 1BR

This one Bedroom apartment is in a riverfront colonial mansion built by oilcloth baron and philanthropist Deborah Ball Powers in the early 19th century. The apartment is modest: full kitchen, dining room downstairs and BR / bath up. But the grounds are grand: 2 acres of Hudson river waterfront - comes with shared use of canoes, croquet or badminton and other games for the lawn, and bikes you can ride to historic local destinations.

Guest favorite

An outdoor deck is shown, featuring a glass table surrounded by four light green chairs. An umbrella provides shade over the seating area. In the background, an above-ground pool is positioned alongside lush greenery and trees, creating a private atmosphere.

Cottage in West Sand Lake

4.99 out of 5 average rating, 108 reviews

Cozy Cottage with Pool

This is a 2 bedroom, 1 bathroom cottage located on a quiet street close to town. House is in walking distance to Reichards Lake. The home is bright with an open living space and vaulted knotty pine ceiling. Lovely eat in kitchen. Bathroom with shower/ tub combo as well as washer and dryer. Outdoor space includes a fenced in back yard, above ground swimming pool and sun deck. Patio table, gas grill and outdoor fire pit.

Guest favorite

A charming cabin exterior features a wooden porch with a yellow door. Stone pathways lead to the entrance, surrounded by landscaped greenery. Natural lighting highlights the rich wood beams and inviting seating area, while vibrant foliage of the forest provides a serene backdrop.

Cabin in East Nassau

4.98 out of 5 average rating, 119 reviews

Design Lover’s Blue Cabin

Blue Cabin is a cozy, design-forward retreat between the Capital Region and the Berkshires. Enjoy vaulted wood ceilings, a forest-green kitchen, and a spa-style bath. Outside, unwind in the covered lounge with U-shaped sectional, charcoal grill, and TV—or explore the backyard, where a creek runs through and a seasonal flower garden blooms. Peaceful, private, and perfectly located for both rest and adventure.