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

4.9 out of 5 average rating, 164 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

G$33,001 GYD 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.

Jul 6 – 13

G$25,945 GYD 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!

Jan 9 – 16

G$26,812 GYD per night

Guest favorite

Guest suite in Red Hook

4.89 out of 5 average rating, 294 reviews

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.

Nov 27 – Dec 4

G$34,713 GYD per night

Superhost

Farm stay in Red Hook

4.78 out of 5 average rating, 252 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!

Jun 11 – 18

G$24,236 GYD 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.

Mar 29 – Apr 3

G$32,692 GYD per night

Guest favorite

Home in Tivoli

4.92 out of 5 average rating, 117 reviews

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.

Sep 1 – 8

G$58,239 GYD per night

Guest favorite

Guest suite in Kingston

4.98 out of 5 average rating, 213 reviews

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..

Mar 2 – 9

G$30,556 GYD 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 12 – 19

G$26,716 GYD per night

Guest favorite

Guesthouse in Germantown

5.0 out of 5 average rating, 134 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).

Jan 23 – 30

G$29,327 GYD per night

Guest favorite

Farm stay in Ancram

4.95 out of 5 average rating, 264 reviews

Relaxing secluded stay with loving social animals.

Do you love nature, animals, and spa comforts? Then this is the perfect place for you! This is a fully finished, private area ground-floor walk-out, in the basement of the main house. Right outside your front door is 800 acres of hiking trails. You are surrounded by a mature forest, with loving and social goats, geese, ducks, kitty, and pups. To enhance this private retreat there are a hot tub and sauna steps from your door.

Sep 1 – 8

G$33,331 GYD per night

Guest favorite

Tiny home in Saugerties

4.94 out of 5 average rating, 217 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

Feb 5 – 12

G$25,523 GYD per night