Holiday rentals in Annandale-on-Hudson

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Top-rated holiday rentals in Annandale-on-Hudson

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite

The living room features a spacious gray sofa adorned with a striped throw, complemented by a wooden table and an elegant chandelier overhead. Natural light enters through large windows, highlighting the decorative fireplace and vintage ceiling details. A desk and plant can be seen in the adjacent area.

Flat in Kingston

Explore Historic Uptown Kingston from the Bau Guesthaus, C

Sit on the front porch watching people go by and gaze at the old Dutch church. This unit is in a townhouse built in the 1890s with vintage details including ornamental ceilings, a bay window and decorative fireplaces alongside contemporary artwork. Entire 900sqf 1st floor unit. Includes 1 bedroom(Queen), private kitchen/dinning room, living room and a bathroom. The townhouse is restored with beautiful, vintage details but also with all the comforts of modern living like high speed Wifi, digital thermostats and entry to the home via smart lock. *additional one time fee of $25 to set up air mattress for 2 guests. All guests are welcome to use all facilities on our property; including our backyard. The apartment is in the heart of historic uptown Kingston. It’s within walking distance of many of the sights of the uptown Stockade district of New York’s first capital. Explore the weekend farmers’ market, restaurants, museums, and music venues. The Bau Guesthouse is easily accessible by bus or by car. It is 7min walk from the Kingston Trailways bus stop and 5min drive from I-87 throughway exit 19. Parking on our street is metered Monday - Saturday 9am to 5pm. Also free street parking is available just around corner from us.

4.97 out of 5 average rating, 696 reviews

Top guest favourite

A charming cabin is set against a backdrop of trees, featuring a blue exterior and a sloped metal roof. Reflections of the cabin are visible in the calm surface of a nearby pond. A small deck with steps descends into the water, enhancing the outdoor scenery.

Home in Rhinebeck

Slate Cabin - Stylish Country Escape x Rhinebeck

This designer cabin blends natural materials and modern finishes. — sophisticated & cozy. Gaze at (or swim in!) the stunning spring-fed pond steps from the house. Lounge on the deck or enjoy coffee in the sunroom. The interiors feature three bedrooms, two full bathrooms, living room with chic and cozy furniture and wood burning fireplace, and fully appointed kitchen that's a joy to cook in. Entertain your family & friends at the table for 10 and continue out to the grounds, beverage in hand.

4.98 out of 5 average rating, 132 reviews

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

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

4.84 out of 5 average rating, 282 reviews

Top guest favourite

Home in Tivoli

Beautiful & comfortable 3 Bedroom Home

We invite you to stay at our new home in Tivoli, NY, an amazing gem of a town close to everything the Hudson Valley & Catskills have to offer. This property is amazing year-round, just a short walk to the village, and is well-maintained inside and out. Super comfortable, an easy place to gather and relax. The heated in-ground pool is typically open between April thru October. We often host families, people visiting Bard or Kaatsbaan, explorers, and anyone wanting an escape from the busy life.

4.97 out of 5 average rating, 110 reviews

Top guest favourite

The exterior of the farmhouse is presented, showcasing its Romantic Carpenter Gothic style. A trellised porch is visible, surrounded by lush greenery and trees. A fieldstone wall frames the front yard, adding character to the historic property.

Home in Red Hook

The Cat's Meow Farmhouse Red Hook Rhinebeck

CATS Welcome! DOGS MUST BE APPROVED UPON REQUEST! Not for those allergic to cats. An 18th-century Carpenter Gothic style farmhouse c.1840 style with a trellised porch overlooking fields. Sleeps six in 3 bdrms. The house combines modern utilities (2 full baths, WIFI, smart TVs, washer/dryer, & full kitchen) antique furniture & two 18th-century stone fireplaces . Rural, yet only 1.6 mi. to village with many eateries, 2.8 to grocery store. 8.5 to Rhinebeck, 6 to Bard, and 2 to Aerodrome.

4.98 out of 5 average rating, 102 reviews

Guest favourite

A spacious hot tub sits by the tranquil waterfront, with serene views of the creek and surrounding trees. Adirondack chairs are positioned nearby, inviting relaxation under clear blue skies.

Home in Lake Katrine

Waterfront Cottage - Hot Tub, Kayaks and Fire Pit

Welcome friends to our beloved waterfront cottage right on the Esopus Creek, in the beautiful Catskills! Whether you’re seeking a peaceful retreat, fun for the family, or a romantic escape, our 2-bedroom home is your perfect Catskills destination. With kayaks for adventures on the creek (Spring through Fall), a firepit with water views, outdoor dining with a grill, and located close to lots hiking and nearby towns, like Woodstock and Saugerties, you'll only wish you could stay here longer!

4.95 out of 5 average rating, 109 reviews

Top guest favourite

The exterior view of the guest house is framed by a large tree, showcasing the red brick barn-style structure. Outdoor seating areas are visible, along with a shaded patio featuring a red umbrella. The surrounding lawn is well-kept, leading to fenced paddocks in the background.

Farm stay in Red Hook

Sackett & Van Dam Guest House @ Little 9 Farm 1706

Named one of "The 10 Best Remote AirBnBs for an Escape From Reality" according to the author of 'Leave the World Behind' First Floor Open Space includes a fully equipped Kitchen (Viking Range, Dishwasher, Washer, Dryer, FridgeFreezer, Caesartone Counters), a Dining Room for 8 and a Living Room with Decorative Fireplace, Smart TV & Cable Second floor has 2 Bedrooms: One with a King bed overlooking the paddocks One with 2 Queen beds and a Desk overlooking the pool One bathroom with shower.

4.98 out of 5 average rating, 179 reviews

Top guest favourite

An open-concept space features wooden beams and large windows, filling the area with natural light. A dining table with six chairs is positioned centrally. A cozy seating area includes a sofa and armchair, while a staircase leads to the loft bedroom above.

Cottage in Rhinebeck

Fabulous Lemon Cottage in Rhinebeck, NY

This cozy, clean, and light-filled cottage with its bedroom loft provides a perfect getaway anytime of the year. When you do venture out, you're in the heart of it all; only a few miles from Rhinebeck village, but also close to Red Hook, Bard, Kingston, Woodstock, Hudson, etc. Use our guidebook to explore the area, or choose to stay in at this quiet, private cottage with views of the woods. LGBTQIA+ friendly. All people from all cultures and backgrounds, without exception, are welcome.

4.99 out of 5 average rating, 185 reviews

Top guest favourite

A cozy living area is highlighted by two wooden chairs positioned around a central rug. A gas fireplace provides warmth, with shelves filled with books flanking the fireplace. Soft light filters in through large windows, illuminating the space.

Home in Germantown

Private Hudson Valley Loft on 200 Acre Horse Farm

Escape to Germantown, explore the farm’s 200-acres and visit the horses. they love carrots and visitors! Bright and airy open floor plan loft in Germantown, NY. Once an apple storage barn, this recently remodeled loft features two bedrooms, each with its own private bathroom, beautiful original pine floors, gas fireplace, central air, cook’s kitchen, and a large outdoor deck overlooking open fields and a pond. We are dog friendly up to 2 dogs. There is a $50.00 fee per dog. NO CATS.

4.99 out of 5 average rating, 375 reviews

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

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.

4.95 out of 5 average rating, 503 reviews

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

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.

4.93 out of 5 average rating, 113 reviews

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

A perfect Hudson Valley getaway.

Spacious and relaxing environment for adults ,with cathedral ceiling in livingroom & skylight in kitchen. It is not suitable for children, no childproofing.. 1 mile from the center of Red Hook, with off street parking & private entrance. Big livingroom w/ TV in the armoire. Wifi ready. Full kitchen , bathroom w/roomy shower. Large bedroom / closet space. Washer & dryer available. 4 miles from D C Fairgrounds. Minutes to Bard College , Taconic Pkwy, NYS Thruway

4.99 out of 5 average rating, 120 reviews