Holiday rentals in Annandale-on-Hudson

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Top-rated holiday rentals in Annandale-on-Hudson

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Top guest favourite
A bright living area features large colonial-style windows allowing natural light to fill the space. The decorative fireplace is paired with a compact coffee table, a comfortable gray sofa, and simple wooden dining seating, enhancing the welcoming ambiance.
Flat in Kingston
4.98 out of 5 average rating, 730 reviews

Colonel Hasbrouck’s 1735 Stone House, Street Level

Step through the red door into a designated landmark dating from 1735. Light from tall colonial Dutch windows reflects off the hand-restored wide-board floors and the decorative fireplace. There’s a backyard view through the split Dutch door. The apartment is cleaned according to Airbnb's enhanced cleaning protocol. It has a small Roku TV, and an infant pack and play, high chair, and bouncer seat. Internet is powered by the fastest tier available. Downstairs you'll find a bright and airy living room in the front, the light from the tall colonial dutch windows reflected off of the hand-restored original wide-board floors. Past the large decorative fireplace is a newly renovated full kitchen and dining nook, with a backyard view through the split dutch door. Upstairs is a modest but modern bathroom with a heated towel rack, and two bedrooms, each with a 12" queen-sized memory foam mattress on a solid steel frame. For your comfort, the apartment has its own heating and cooling controls, with separate programmable thermostats for upstairs and downstairs. Check-in is done automatically via keypad (your personal code is sent via email when you book), but we’re right next door to answer your questions or point you to a good restaurant. The Colonel Abraham Hasbrouck House is in the historical Stockade district. At the center of Kingston, the first capital of New York State, the neighborhood is charming and walkable with some great restaurants, bars, cafes, and shops. Here's how most folks get here. By bus: 5 minutes on foot from the Trailways bus terminal, about 2 hours from the Port Authority By car: 3 minutes from exit 19 of I-87, about a 90-minute drive from the GW bridge. By train: 20 minutes by car from the Rhinecliff Amtrak station, about 2 hours by train from Penn Station If you're coming by car, parking is free on our street, and finding a spot is usually pretty easy on weekends and weekdays after 5pm. Otherwise, there are 3 paid municipal lots you can use, all within two blocks. We've taken a lot of care to preserve the original wide-board floors, but since they came from trees that started growing before Henry Hudson came up the river, they're crooked and creaky. Take care when walking on them and the stairs to the bedrooms upstairs, and feel free to use the slippers we've provided.

Top guest favourite
A cozy bedroom features a spacious bed with layered bedding. A gallery wall of framed art pieces adds visual interest. Natural light filters through a window with shutters, illuminating the warm wood floors. An electric fireplace and a potted plant provide a touch of comfort.
Flat in Kingston
4.97 out of 5 average rating, 337 reviews

The Ivy on the Stone

The oldest house you can stay at in the historic heart of Kingston! Walkable! This landmark 1680 stone house has been featured in Upstate Diary and Houzz. Enter this 350 sq ft luxe apartment through a secret garden and a shared porch. The private spa-like bathroom features a clawfoot tub, and rain shower. Featuring an organic queen bed, an electric fireplace, workspace, William Morris wallpaper, and a Nespresso maker. If you want to stay in the larger house visit: https://abnb.me/EexspArCAIb

Guest favourite
A spacious room features a full-size bed with a patterned quilt and nearby bedside table. Natural light enters through large windows, complemented by elegant curtains. An inviting seating area includes a sofa and a small side table. A work desk and dresser provide additional functionality.
Flat in Red Hook
4.85 out of 5 average rating, 258 reviews

A&A's Upper Red Hook

This comfortable, light-filled apartment is located under 10 minutes from Bard College, Fisher Center and Red Hook Village. Private entrance leads to the space that includes the full-size bed (not queen) and a queen-size sofa/futon for additional guests. The ensuite bath features a lovely tiled shower. A kitchenette includes large air fryer, microwave. The dining/work space is a mahogany table. Mesh WiFi. Roku TV. Air conditioning, off street parking round out the features. An easy choice 4 you

Top guest favourite
A comfortable living area features a beige sofa with decorative pillows, accompanied by two side tables and lamps. A floral artwork hangs above the sofa, while a cozy armchair is positioned nearby on a light area rug.
Guest suite in Red Hook
4.99 out of 5 average rating, 109 reviews

A perfect Hudson Valley getaway.

Spacious, comfortable and relaxing environment for adults, ready to make you feel right at home. It is not suitable for children, no childproofing.. Just 1 mile from the center of Red Hook, with off street parking & private entrance. Big livingroom w/ TV hidden in the armoire. Wifi ready. Full kitchen & large bathroom w/roomy shower. Large bedroom / closet space. Washer & dryer available. 4 miles from Dutchess County Fairgrounds. Minutes to Bard College , Taconic Pkwy, NYS Thruway

Guest favourite
A functional kitchen area features gray cabinetry and a white countertop, complemented by a window allowing natural light. A small dining table with chairs is set nearby, adorned with a vase of flowers. A coffee maker and kitchenware are also visible on the counter.
Cottage in Rhinebeck
4.82 out of 5 average rating, 103 reviews

Blue Cottage in Rhinebeck

* private and quit with few minutes walk to a lake ( unfortunately not for swimming). * walking trails around the property. * 5 minutes drive to the Dutchess County fairground. * 5 minutes drive to Kingston-Rhinecliff bridge. * Seven minutes drive to the village of Rhinebeck. * twenty to twenty five minutes drive to Woodstock * Twenty minutes drive to the Omega institute. * twenty to twenty five minutes drive to the Culinary Institute of America. * ten minutes drive to Bard College.

Top guest favourite
The open living area features tall windows that provide ample natural light. A comfortable sofa is situated beside a wooden coffee table, with a dining table set for four in the background. Modern appliances and a stylish ventilation hood enhance the kitchen space.
Flat in Kingston
4.97 out of 5 average rating, 147 reviews

Rondout Rendezvous

Enjoy the historic Rondout district of Kingston while relaxing in this beautiful, one-bedroom, one bath unit on the first floor of a brick building from 1900. Historic charm meets modern amenities, with 12' ceilings, in-floor heating, and an open concept kitchen, living and dining area across the street from the Hideaway Marina on the Rondout Creek. Take a relaxing walk along the water to the historic waterfront area on Broadway for dining, shopping or a boat ride on the Hudson River.

Top guest favourite
A spacious interior features exposed wooden beams and light-colored flooring. Large windows allow natural light to illuminate the room, highlighting comfortable seating areas and a dining table. A staircase is visible, leading to the upper level, enhancing the open and airy design.
Home in Germantown
4.95 out of 5 average rating, 461 reviews

Rustic Swedish Barn/Featured in Airbnb Magazine

Enjoy expansive views of the Catskill Mountains from this renovated but rustic Scandinavian barn. Featured in many magazines and catalogues, including AirBnB Magazine. Walk the property, with its big open field, an organic orchard, walking paths, and flower gardens. A large private pond is swimmable (after heavy rains it does get muddy). The Barn has central heat and air conditioning. A full bathroom features an antique bathtub. Enjoy dining inside, or outdoor grilling and dining.

Guest favourite
A modern kitchen features sleek white cabinetry and stainless steel appliances, including a gas stove and refrigerator. An island with black countertops is centered in the space, complemented by three black stools. Large windows provide natural light, enhancing the bright and airy atmosphere.
Guest house in Red Hook
4.94 out of 5 average rating, 103 reviews

Private Cottage, Walk to Restaurants and Shops

Beautifully renovated modern cottage in the village of Red Hook has modern amenities, hardwood floors, and an open floor plan. The cooks kitchen has an island and high-end appliances. Walls of windows and doors bring in lots of light and there's a private patio out back. Bathroom has large walk-in shower. Bedroom has a king bed (or two twins) and a recliner for reading. A 3 minute walk from center of Red Hook and Bard Shuttle. 10 minute drive to both Bard College and Rhinebeck.

Top guest favourite
The entrance of the loft apartment is framed by a charming overhang and features a decorative door in a soft shade of purple. A pathway made of stone leads to the door, bordered by landscaped gardens and a flowering tree, enhancing the welcoming appeal.
Guest house in Germantown
4.99 out of 5 average rating, 252 reviews

The Loft

This beautiful loft apartment is located in the heart of Germantown- just 0.3 miles from Otto's Market (groceries and deli), And Universal Cafe. " farm to table global inspired classics." We offer tea & coffee in the loft, parking, yard access, wifi, basic amenities, full kitchen and a smart TV that has a fire stick with access to Amazon Prime and Netflix (no cable).

Guest favourite
The exterior of the Strand House is showcased, featuring a historic brick facade with large windows. A prominent sign reading 'STRAND HOUSE' is displayed above the entrance, which is accessed by a set of steps. Potted yellow flowers are placed near the entrance.
Flat in Kingston
4.92 out of 5 average rating, 297 reviews

Historic Strand House - Unit 2 Woolsey Suite

Brand new luxury apartments in a restored historic building located in the heart of the historic Rondout District in downtown Kingston. A five minute walk from the waterfront, restaurants, bars, galleries, shops and marina. The Strand House consists of 4 units: (2) studios and (2) two-bedrooms all individually decorated and thoughtfully curated.

Top guest favourite
The cottage features a warm, rustic exterior with wooden siding and a sloped roof. Surrounding greenery includes tall grasses and shrubs, enhancing the natural setting. Sunlight casts gentle shadows on the facade, while a decorative weathervane adds charm to the rooftop.
Cottage in Tivoli
4.97 out of 5 average rating, 228 reviews

Clausterhaus

The "cozy cottage" with a rustic feel but all the amenities of a fine hotel- exposed beams-goose down sofas and chairs- old fashioned gas burning stove to keep you warm in the cold winter months. *Please take note that we are not currently serving breakfast due to the pandemic but hope to resume when it is safe to do so.

Top guest favourite
The exterior of the house showcases a modern rustic design, featuring a stone and wood façade. Large picture windows reflect the surrounding nature, while an outdoor fire pit is surrounded by several Adirondack chairs on a grassy area. A dining table and chairs are positioned nearby.
Home in Rhinebeck
5 out of 5 average rating, 243 reviews

Eagle Rock House

FRESH AIR • SMOKE FREE • ALLERGY FREE Early Check In & Late Check Out! Eagle Rock House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space.

Popular amenities for Annandale-on-Hudson holiday rentals