Vacation rentals in Annandale-on-Hudson, Red Hook

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Top-rated vacation rentals in Annandale-on-Hudson, Red Hook

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Apartment in Red Hook

4.86 out of 5 average rating, 240 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

Guest favorite

Guest suite in Rhinebeck

4.91 out of 5 average rating, 453 reviews

Contemporary Rhinebeck Private Village Retreat

Quarters covid sanitized.Huge bedroom,CalKing bed.(twin bed avail.upon request,$30/day xtra for 2 people,$55 for 3 people w/extra bed)bathroom,(NO Kitchen)has coffeemaker, fridge,TV,Wifi,A/C, private patio & garden. No pets.PLEASE NOTE:Pic shows front of house so guests can find it,quarters on lower level to private entrance,*See Pics.Close to hiking, shops,26 restaurants,Omega, Bard College, Dutchess Fairgrounds *babies ok. No toddlers or kids under 7. June/July,Aug/Oct-wknds 2 day minimum

Top guest favorite

Cottage in Rhinebeck

4.99 out of 5 average rating, 151 reviews

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.

Top guest favorite

Home in Saugerties

4.98 out of 5 average rating, 131 reviews

Sexy Abode in the Coolest Town - Saugerties, NY

GlassCo Hill is the newest addition to our eclectic collection of getaways at the Brigham Group - a family owned and run hospitality group. GlassCo Hill is centrally located in Saugerties, NY; one of the coolest small towns in the Hudson Valley. It is a sexy little two bedroom home that is perfect for a quick getaway or even for longer stays! The fully equipped kitchen will make your stay even more comfortable. Centrally located to all the Hudson Valley has to offer!

Top guest favorite

Guest suite in Woodstock

4.99 out of 5 average rating, 160 reviews

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.)

Top guest favorite

Cottage in Red Hook

4.98 out of 5 average rating, 250 reviews

CoZy Newly Renovated Cottage in Red Hook Village

'Solas Na Gréine' (Meaning 'light of the sun' in Irish) - Beautifully renovated private cottage located in the Village of Red Hook, New York. A perfect Hudson Valley getaway anytime of the year. Just 2 blocks (3 minute walk) to the town's center with wonderful cuisine, shops & small town charm. A short 5 minute drive to Bard College Campus, Hiking Trails, Orchards, Farms, & Wineries. Come relax, enjoy & explore upstate NY, just 90 miles from NYC.

Guest favorite

Tiny home in Saugerties

4.95 out of 5 average rating, 292 reviews

Gorgeous Tiny House with Mountain View

Enjoy our little cabin and feel off the grid, without being far from the charming village of Saugerties and close to Woodstock. Enjoy the beautiful Catskills area and retreat in our beautifully renovated “tiny haven” ... complete with a Mountain View! Ac cools beautifully in summer! The Haven at Blue Mountain! ******Can also be booked together with the Main House on the property, listed as Blue Mountain Haven! https://abnb.me/SMQTSu5LQpb

Guest favorite

Guesthouse in Tivoli

4.91 out of 5 average rating, 173 reviews

Tivoli Star Gazing Cabin

Down a long driveway, set amongst 100 year old trees and meadows, the cabin offers time in the quiet country though only minutes to the lively village of Tivoli. With a wrap around porch for morning coffee, fire fly viewing or star gazing. It has a soaking tub, with a hand held shower. The cabin is part of our family compound of a main house and a small garden hut. Each property has an independent outdoor space for relaxing and privacy.

Top guest favorite

Apartment in Hudson

4.97 out of 5 average rating, 144 reviews

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

Loft in Kingston

4.97 out of 5 average rating, 129 reviews

Villa Costello,

Welcome to our stunning loft apartment in East Kingston, a hidden gem nestled between the captivating Catskill Mountains and the glistening Hudson River. This location offers more than just a stylish place to stay. With historic attractions, a plethora of fun activities, and delectable dining options. your weekend getaway will be nothing short of memorable. Book your stay now and experience the beauty of East Kingston for yourself!

Top guest favorite

Guesthouse in Germantown

4.99 out of 5 average rating, 212 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 favorite

Cottage in Tivoli

4.97 out of 5 average rating, 211 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.