Holiday houses in Castleton-on-Hudson

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Top-rated holiday rentals in Castleton-on-Hudson

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Guest favourite
A charming courtyard is surrounded by greenery and blooming flowers. A shaded area features a comfortable seating arrangement with neutral-colored cushions. Additional seating is available in the background under canopies, providing an inviting space for relaxation.
Guesthouse in Troy
4.93 out of 5 average rating, 670 reviews

Whimsical Carriage House & Enchanting Courtyard

Welcome to your boutique retreat in the heart of downtown Troy! This cozy second-floor studio, designed by a local artist, is tucked away in a standalone Carriage House with a private entrance next to a whimsical mural by local artist Kayla Ek, and a lush New Orleans-inspired courtyard. Just steps from Troy’s best dining, art, nightlife, and wedding venues—and less than a block from the RPI approach—this gem is perfect for a romantic getaway, solo escape, or stylish stay while visiting the area.

Top Guest favourite
Apartment in Center Square
4.93 out of 5 average rating, 227 reviews

Historic, Spacious Mansion Suite

Welcome to the Mansion Suite, a newly renovated historic gem in the heart of Center Square. Through a private entrance, down a long foyer, you'll discover the grand Oak Room, an expansive living/dining room with dramatic fireplace mantel, paneling, beamed ceiling, stained glass windows. Adjacent to the lounge, is a stylish and fully equipped kitchen with new stainless steel appliances. Both bedrooms have new queen beds, beautiful natural woodwork and overlook a private and quiet courtyard.

Top Guest favourite
The charming cottage is set within a lush garden, featuring a gently curved stone pathway leading to the front door. Surrounding greenery includes well-maintained shrubs and trees, creating a tranquil and inviting outdoor setting.
Cottage in Kinderhook
4.98 out of 5 average rating, 248 reviews

The Cottage on Sylvester Street

The Cottage on Sylvester Street welcomes guests looking for a relaxing weekend or longer stay in a small-village setting. Located at the heart of the historic Village of Kinderhook, this stylishly renovated house is located amongst Kinderhook's collection of historic architectural gems. Within easy walking distance are eateries, wine and beer bars, The School I Jack Shainman Gallery, historic sites, the farmers' market plus farm stands, and quiet, scenic roads perfect for walking and cycling.

Guest favourite
The studio features a queen size memory foam bed positioned against a stylish wall. A work desk and chair are nearby, with a round mirror reflecting light. The kitchen area includes a bar-height counter with two stools, blending functionality with mid-century modern design.
Guest suite in Center Square
4.91 out of 5 average rating, 370 reviews

Garden Apartment in Historic Center Square Home

Welcome to our charming studio in the heart of Albany's Center Square. Nestled in one of the oldest homes in the neighborhood, the space has been restored to blend history with modern convenience. Recently renovated, it features a modern bathroom with rain shower. The décor is a nod to mid-century aesthetics. This cozy studio is a stone's throw away from Albany's main attractions within easy walking distance. Experience a unique blend of past and present in this delightful Albany retreat.

Top Guest favourite
A spacious living room features two upholstered chairs and a round coffee table topped with fruit. A decorative area rug in warm colors covers the floor, while a large, modern television is mounted above a decorative fireplace. Bookshelves are visible in the background.
Apartment in Nassau
4.92 out of 5 average rating, 101 reviews

A Haven of Rest Beautiful Historic Tranquil Suite

Step back in time into a fully appointed 2nd floor suite in a stately 1830 Federal Home. Rest Haven Estate is a country manor with a wonderful history that only adds to its charm. Private entrance. Full kitchen, bath, large living room with 2 twin sofa sleepers, cozy private bedroom with queen bed. High speed internet. Cable TV, Microwave, Stove, Refrigerator, Desk, Coffee Maker Located across from Albany- Hudson Electric Trail for walking, biking, cross country skiing, and snow shoeing.

Top Guest favourite
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, 267 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 favourite
An open floor plan reveals a spacious apartment with yoga slings hanging from the ceiling. A vintage red love seat is situated in a reading loft, while a kitchen area is visible towards the back. The flooring features an eclectic mix of textures and colors.
Loft in Troy
4.95 out of 5 average rating, 278 reviews

Large bohemian loft: The Chromium Compound

Large storefront converted to colorful open plan apartment in the heart of downtown Troy. Blocks away from RPI, and steps away from most of Troy's nightlife. Warning: this urban bohemian experience may bring back memories of Williamsburg Brooklyn or Downtown LA in the 90's. Note that sounds from outside and adjacent apartments may bother light sleepers, so don't book this one if that is a concern for you. Also parties are not allowed because of close neighbors! Thanks!

Top Guest favourite
A spacious kitchen features modern appliances and elegant cabinetry. A gas stove is positioned beneath a stainless-steel hood, while a farmhouse sink is complemented by stylish fixtures. Light-colored countertops are paired with a herringbone backsplash, creating a fresh and inviting cooking space.
Home in Delmar
5 out of 5 average rating, 113 reviews

Rustic Farmhouse Meets Chic!

This stylish and spacious place to stay is perfect for family trips! Enjoy your privacy in this completely renovated three bedroom house, with full bathroom, and fully equipped kitchen. Located in the heart of Delmar, within walking distance to restaurants, bars, Stram Center for Integrative Medicine, and less than 10 minutes drive to Downtown Albany, Interstate 87 exit, 12 minutes drive to Albany Medical Center, and 20 minutes from the Albany International airport.

Top Guest favourite
The living area features a comfortable seating arrangement with a patterned armchair and a light-colored sofa accented by a vibrant throw. A side table is positioned next to the sofa, and a wall clock adds a decorative touch, while wooden flooring enhances the cozy ambiance.
Apartment in Troy
4.96 out of 5 average rating, 124 reviews

Adorable Apartment - Near Emma Willard, RPI, Troy

Welcome to Cheri's house! You'll enjoy a private 1 bedroom apartment including a full size bed in the bedroom, living room with pull-out sofa and smart TV, full kitchen, bathroom and bonus work space or dining room. Off street parking, free WiFi and breakfast included. My home is a quick 5 min walk to Emma Willard School, 1.5 miles to RPI, and 2 miles to Russell Sage College. The unit is on the 2nd floor of an owner-occupied house. Please ask me any questions!

Superhost
A welcoming living area features exposed brick walls and a patterned area rug. A vintage-style couch is placed in front of a wooden coffee table. A curtain separates the sleeping area, which is partially visible in the background, revealing a cozy bed.
Apartment in Troy
4.89 out of 5 average rating, 111 reviews

Cool Brick Basement Studio Parking Fast WiFi AC

Cool 1900 brick basement level studio with curtained off sleeping area, fast wifi, tile floors, brick walls, nearly new kitchen, granite countertops, air conditioning & shared laundry. South Central Troy (Washington Park Neighborhood) quiet street, just 1 block to Carmen's Cafe, 3 blocks to Russell Sage, within walking distance to quaint shops, dining, nightlife and everything else Downtown Troy has to offer. Close to R.P.I, H.V.C.C, and Emma Willard.

Top Guest favourite
The spacious bedroom features a king bed adorned with a dark blue throw and neatly arranged towels. Soft lighting is provided by bedside lamps on each side of the bed, while a plant adds a touch of greenery. Two landscape artwork pieces hang above the bed.
Townhouse in Clifton Park
5 out of 5 average rating, 235 reviews

Cozy Stay – King Bed, Soaking Tub & Fire Pit

Cozy winter reset in Clifton Park—perfectly located for easy trips to Saratoga Springs, Albany, Troy, and Schenectady. Sink into a plush king bed, unwind in the soaking tub, and end the day by the fire pit under string lights. Whether you’re here for a quiet getaway, work trip, or a longer stay, you’ll have comfort, privacy, and the space to truly relax. Outdoor movie screen: “available weather-permitting” + two 65" TV indoors for winter nights.

Top Guest favourite
A charming home is set in a serene neighborhood, featuring a white exterior and red shutters. Bright autumn leaves blanket the ground, while colorful trees are seen in the front yard. The house includes a small set of stairs leading to its entrance.
Home in Bethlehem
4.98 out of 5 average rating, 50 reviews

Cozy Renovated Home Near Albany

Newly renovated home just 10 mins from Albany. Perfect for families, couples, or solo travelers. Sleeps up to 5 adults + 1-3 children with 3 bedrooms, 2 queen beds, a twin, toddler bed, and Japanese floor mattress. Modern kitchen, fast Wi-Fi, Smart TV, washer/dryer, and free parking. Near hiking, wineries, museums, Saratoga Race Course, and local attractions. Safe, peaceful neighborhood. A stylish, cozy retreat at an affordable rate!

Popular amenities for Castleton-on-Hudson holiday rentals