Vacation rentals in Annandale-on-Hudson

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Top-rated vacation rentals in Annandale-on-Hudson

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Guest favorite

Tiny home in Kingston

Esopus Creek modern Tiny house Retreat!

Dare to break from the hustle and bustle culture and immerse yourself in the beauty and solitude of our modern spacious brand new Tiny house tucked away on a peaceful dead street on our 13 acres bluestone property located 10 mins from Woodstock and Kingston.You will be steps away from waterfalls on the creek nature trails and a myriad of flora and fauna,sleeps up to 6, masterbedroom and loft has queen beds,loveseat with full bed, one bathroom with shower and updated regular toilet . Close to ski

Guest favorite

Guesthouse in Germantown

The Studio at Pear Farm

Sophisticated large studio has gorgeous light and Catskill Mountain Views Formally an artist studio, it has undergone an elegant renovation. The luxurious bathroom features premium tile and a glass walled shower The kitchen is new, nicely equipped and has a full sized refrigerator. Enjoy outdoor grilling and dining on the private deck. The studio is located on 65 pristine acres fronting directly on the Hudson River. 5 minutes to Germantown. 10 minutes to Tivoli, Hudson or Bard College.

Guest favorite

Rental unit 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 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 for your visit.

Guest favorite

Guesthouse in Kingston

Campfire Cottage: Fireplace, fire pit & no chores!

Escape the city and unwind at this beautifully designed home. Just 90 minutes from Manhattan, this is the perfect place to relax and reconnect with nature, or work remotely. Enjoy downtown attractions, hiking, and the Hudson River Maritime Museum nearby. The home features a cozy living area, full kitchen, electric fireplace, and no chore list for checkout. The yard has a grill and fire pit facing the woods. Book today to retreat to your private house and enjoy the beauty of Upstate New York!

Guest favorite

Guest suite in Red Hook

the farmhouse suite at gallatin farmstead

A 575 sq ft. fully private suite with your own entrance in a beautiful early American eyebrow colonial. The mid-century farmhouse style is highlighted by a darling kitchenette. And don't forget the bathroom hot steam shower! Of note, with a 30$ fee, we can set up a 2nd bed in the suite living room. We're happy to do it, it just takes some time to get together. It's a super comfortable mattress, the same model as the queen bed. We are also cycling happy and offer bike rentals and tours.

Guest favorite

Guest suite in Kingston

Peaceful large Hudson Valley private guest suite

The health and safety of my guests is my top priority! I want to reassure you that the suite is cleaned and sanitized by myself and I am vigilant in upholding these practices. Mid-century home with private entrance guest suite on 5 acres. Queen bed, full kitchen, modern amenities, luxury dishware, flatware and quality linens. Decorated with vintage and modern furnishings contribute to a peaceful retreat. 5 min drive to Kingston, 15 min to Woodstock and Saugerties..

Guest favorite

Home in Tivoli

Entire House with Panoramic Views of The Catskill

Stay at our home located 2 miles from Bard College and the cozy village of Tivoli and less than 10 miles from the trendy towns of Red Hook and Rhinebeck. We have 3 bedrooms and one sleeper couch. Picture windows from all westward facing rooms and our deck provide 60-mile panoramic views of the Hudson Valley and Catskill Mountains. Great for families visiting students at Bard or enjoying nearby visits to Hyde Park. Single level home with complete kitchen and 2 bathrooms.

Guest favorite

Guest suite in Woodstock

Woodstock retreat with hot tub and deck with view

Guest suite in home of long-time Woodstock artist and resident. Separate entrance off 2nd story deck with meadow and mountain views. Space has everything you need for a retreat away from it all – a meditation nook for 2, yoga mats to use inside or out on the deck, hot tub to soak cares away and relax after a day out and about in the beautiful Catskill mountains. Hot tub is in 3-acre backyard with privacy enclosure, so bathing suits are optional (we provide bathrobes.)

Guest favorite

Guesthouse in Germantown

The Loft

This beautiful loft apartment is located in the heart of Germantown- just 0.3 miles from Otto's Market (groceries and deli), 3 minute walk to Gaskins Restaurant, "A charming eatery serving a locally-sourced menu of classic American fare in a rustic dining room." 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 favorite

Rental unit in Hudson

Restored 19th century farm house apartment

Brought back from the original bnb boarding days of the 19th century is our 1 bedroom top floor apartment located on a peaceful country road 15 minutes from downtown Hudson or Red Hook. You can still see the original numbers of the old boarding house on the doors! The house is surrounded by 12 acres of fields and forest that we welcome you to explore. It’s a small homestead with animals, a geo dome greenhouse and garden. Hope you enjoy!

Guest favorite

Guest suite in Red Hook

Quaint Apartment in Red Hook

The suite has a private entrance and is self contained. It includes a kitchenette, small dining area, living area, bedroom and bathroom. The apartment is perched on a hill and located in the town of Red Hook. Head into town for American fare at Flatiron or try an Italian dish at Savonas. Take a drive to the Opus 40 sculpture park or the historic Vanderbilt Mansion.