Holiday houses in Annandale-on-Hudson

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Top-rated holiday rentals in Annandale-on-Hudson

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Guest favourite

Home in Rhinebeck

4.86 out of 5 average rating, 189 reviews

Vibrant Vintage Country House with Backyard

Now booking Fall fun, Halloween, Thanksgiving, Sinterklass and other holiday escapes to Rhinebeck. Chill in a charming Midcentury Modern period rambler on 3 rural acres close to the village. Experienced host and top guest ratings for cleanliness and style. Super zippy internet and places to put the laptop. Outside: a farm field with mowed wildflower walks, a backyard perfect for dining. We carefully follow AirBNB's cleaning and health and safety protocols. Close to all Hudson Valley's foodie, outdoors and cultural offerings. This is a sweet little circa 1968 period rambler on 3 rolling, wild-flowered acres, newly refurbished (with period elements intact) and decorated in a style that is the intersection of Mid-Century modern and Mad Men/Boho chic. It's a nice get-away and centrally located to enjoy all that Rhinebeck and the Hudson Valley has to offer. There are 2 bedrooms with new beds, vintage period dressers and luxury linens, plus a bright and sunny eat-in kitchen. There are 2 separate living rooms ... one with a 50" flat screen TV, the other for music or reading. A separate dining room with views of the field complete the setting. It's nicely country: close to everything, but a 60 acre horse farm is across the street (where some guests board their mounts), deer often in the back yard (and eat my topiaries out front), and a beautiful pheasant or a shy red fox often can be glimpsed in the field on the side of the house. You will pull into the private driveway with easy parking for up to 4 vehicles. The entire house is yours to enjoy. We will have pre-arranged the code to the key box for the front door. In warm seasons there are outdoor chairs to enjoy, mowed trails through the wildflower fields. In the winter, we are less than an hour away from Belleayer, Catamount and Hunter Mountains. As your host, I make sure the house is spotless, filled with coffee and fresh milk, packed with menus and suggestions for local fun. And there is always a helpful hand nearby in case of questions or any issues. The home is located just five minutes from the town of Rhinebeck. Visit the village to discover its restaurants, art movie house, and events at the Fairground. The area is also home to historic homes and heritage sites. This house is 5 miles from the Taconic State Parkway, 7 miles from the Amtrak Station, and is close to everything.

21 – 28 Apr

$1,936 AUD total

Guest favourite

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

15 – 22 Dec

$1,823 AUD total

Guest favourite

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.

29 Mar – 3 Apr

$1,269 AUD total

Guest favourite

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.

16 – 23 June

$1,451 AUD total

Guest favourite

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.

21 – 28 Aug

$1,806 AUD total

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!

13 – 20 Aug

$1,586 AUD total

Guest favourite

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.

26 – 31 Mar

$1,310 AUD total

Guest favourite

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..

27 Feb – 6 Mar

$1,721 AUD total

Guest favourite

Home in Tivoli

4.92 out of 5 average rating, 116 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.

23 – 30 Nov

$3,337 AUD total

Guest favourite

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).

29 July – 5 Aug

$1,392 AUD total

Guest favourite

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

19 – 26 Jan

$1,424 AUD total

Guest favourite

Guest suite in Red Hook

4.93 out of 5 average rating, 382 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.

30 Jan – 6 Feb

$1,585 AUD total