Vacation rentals in Annandale-on-Hudson

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Top-rated vacation rentals in Annandale-on-Hudson

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Guest favorite

Home in Woodstock

4.91 out of 5 average rating, 638 reviews

Dutch Touch Woodstock Cottage

The Dutch Touch captures the best Woodstock has to offer. Be in the Village and secluded at the same time! This Woodstock treasure is surrounded by gardens, with Monet-worthy views, peaceful mountains and swaying pines. It’s your cozy and peaceful home away from home, yet only a short, pretty walk to the very center of the village. Dutch Touch is the "brain-child" of artist, Manette van Hamel, an early Woodstock arts colony resident whose work is held in the permanent collection of the Met. The kind of place one would expect an artist to build: Perfect for a romantic get-a-way or solo retreat. Recline on your own deck beside a sparkling stream, soak up the sun, read a good book, or walk into town and visit the galleries and shops, or zip up the mountain for hikes, a visit to the Buddhist Monastery or a tour of the Byrdcliffe arts colony. Winter visitors will love the open fireplace, and the fresh winter scent of forest, hearth and home.

Nov 27 – Dec 4

R2,512 ZAR per night

Guest favorite

Tiny home in Kingston

4.9 out of 5 average rating, 165 reviews

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

Dec 14 – 21

R3,032 ZAR per night

Guest favorite

Apartment in Rhinebeck

4.99 out of 5 average rating, 161 reviews

Rhinebeck Ridge - A Woodland Studio Retreat

Nature surrounds this tranquil space nestled within a heavily wooded scenic ridge district, far off the road. Near Omega, Rhinebeck Village, Bard, Walkway over the Hudson, hiking, parks, wineries, swimming, antique stores, farmers markets. Newly constructed & lovingly designed by its builder owner, great attention has been given to quality details designed to soothe your soul. Ideal for singles or couples of any orientation wishing to elegantly commune with nature with all the comforts of home.

May 20 – 25

R2,916 ZAR per night

Guest favorite

Apartment in Red Hook

4.85 out of 5 average rating, 192 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 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.

Jun 9 – 16

R2,373 ZAR per night

Guest favorite

Guesthouse in Kingston

4.94 out of 5 average rating, 133 reviews

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!

Nov 13 – 20

R2,264 ZAR per night

Superhost

Farm stay in Red Hook

4.78 out of 5 average rating, 254 reviews

Farmland Tranquility at The Greig Farm Schoolhouse

Welcome to Greig Farm, a family-run farm since 1942! The Schoolhouse is part of the farm's west homestead, where it sits between our south barn, a plant nursery, and a beautiful pond filled with hundreds of koi fish. We're an active fruit and vegetable farm, open to the public all year long. In the warm months (May-Oct), come pick-your-own fruit and vegetables. Our farm market has a full breakfast/lunch menu and tons of local produce, meat, and other groceries if you'd prefer to cook!

Sep 18 – 25

R2,494 ZAR per night

Guest favorite

Cottage in Rhinebeck

4.99 out of 5 average rating, 120 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 "downtown" Rhinebeck, but also close to Red Hook, 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.

Oct 11 – 18

R4,412 ZAR per night

Guest favorite

Guest suite in Rhinebeck

4.91 out of 5 average rating, 382 reviews

Contemporary Rhinebeck Private Village Retreat

Quarters covid sanitized. Huge bedroom, Cal King bed. (twin bed avail.upon request, $30/day xtra for 2 people, $55 for 3 people w/extra bed)bathroom,(NO Kitchen)but has coffeemaker, fridge, TV,Fast Wifi, A/C, private patio w/ 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 allowed. No toddlers or kids under 7.

Sep 4 – 9

R3,012 ZAR per night

Guest favorite

Guesthouse in Germantown

4.96 out of 5 average rating, 188 reviews

Luxe Guest House Retreat

Welcome to the Guest House nestled in the woods. We designed this lush and light-filled studio with peace and luxury in mind. Situated across from apple orchards, it sits ten minutes from Hudson and ten minutes from Germantown, you get the best of both worlds: country living with two amazing destinations close by. Ideal for a romantic getaway, or to be close to the sights and sounds but can retreat to natural beauty. A true sanctuary from the City.

Aug 16 – 23

R2,454 ZAR per night

Guest favorite

Guesthouse in Germantown

5.0 out of 5 average rating, 136 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), 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).

Dec 27 – Jan 3

R2,818 ZAR per night

Guest favorite

Tiny home in Saugerties

4.94 out of 5 average rating, 218 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! “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

Sep 9 – 16

R2,266 ZAR per night

Guest favorite

Guest suite in Red Hook

4.93 out of 5 average rating, 383 reviews

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.

Feb 21 – 28

R2,658 ZAR per night