Holiday rentals in Beekman

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Top-rated holiday rentals in Beekman

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Superhost

Home in Hopewell Junction

4.93 out of 5 average rating, 28 reviews

Cabin Oasis in the Woods

The Cabin at Hopewell is a spacious, serene, and comfort-first home in the Hudson Valley. This 2-acre property features mature oak trees, a creek, a 2-story wrap-around deck, a heated saltwater pool (May to September!), a hot tub, and all of the amenities you need for a getaway. The home features natural hardwood floors throughout, spa-like bathrooms, extra-large windows to bring the outdoors in, 2 working spaces, and 2 living areas. You'll love this contemporary cabin with old-school character.

Guest favourite

Tent in Poughquag

4.87 out of 5 average rating, 15 reviews

Maybrook Farm "The Ridge"

Soaring view of Hudson Valley from tent on 100 Acre Farm - Direct Access to Empire Rail Trail - Fishing at our Pond! Walk to Appalachian Trail! Enjoy the stars at night and beauty of hills and valley from your canvas tent equipped with bed. Drive up or come by bike to private entrance to the farm from the Empire Rail Trail with a locked gate. The pond has a dock, there is a seasonal babbling brook, walking trails, wildlife. Fire pit, picnic table, outhouse bathroom. Rustic, simple, beautiful!

Guest favourite

Guest suite in Dover Plains

4.91 out of 5 average rating, 317 reviews

Hoppy Hill Farm House

Enjoy the simple country life in this historic farmhouse. Watch the sun rise over the breathtaking mountain views from the front porch while sipping a cup of coffee/tea. For the more adventurous, there are lots of Appalachian Trail hiking opportunities, and nature preserves to enjoy. Plenty of quaint towns near-by: Kent, Millbrook, Amenia, Wassaic for great food, coffee shops, antiques, parks, breweries and vineries. Inside, you will feel right at home in this comfortable one bedroom apartment.

Top guest favourite

Flat in Verbank

4.96 out of 5 average rating, 147 reviews

Large, private apartment in scenic Hudson Valley

We are located right in the middle of the Dutchess County so access to all points is convenient. Many attractions are: historical Hyde Park, Walkway Over The Hudson, Culinary Institute, Vassar & Marist colleges, wineries, breweries, the quaint towns of Millbrook & Rhinebeck, Dutchess County Fairgrounds, and The Links At Unionvale golf course and banquet hall. Great for couples, adventurers and business travelers who love activity but appreciate a comfortable quiet place at the end of the day.

Superhost

Guest suite in Lagrangeville

4.86 out of 5 average rating, 149 reviews

Renovated 1840 Collins Estate Private East Wing

The 1840 Collins Estate took 60 men three full years to construct. The rental is a private, locked East Wing of the home. Fully refinished with modern comforts; bedding, mattresses, bathrooms, coffee bar and more. The home is centrally located near the Links at Union Vale(1 mile), Millbrook, Rhinebeck, Beacon, Poughkeepsie and colleges. Historic sites and festivals abound. Many great restaurants nearby due to proximity to Culinary. Perfect hotel efficiency style getaway cared for with pride.

Top guest favourite

Guest suite in Wappingers Falls

4.8 out of 5 average rating, 111 reviews

Private ground floor guest suite in Hudson Valley

Newly renovated private, ground floor guest suite returning for 2025 rentals! Br, full bath, large LR w/big TV/frig/mw/coffee in centrally located area in the heart of Hudson Valley. Walk to Dutchess Rail Trail/Uber accessible/self ck in. Close to Poughkeepsie, Beacon, Vassar/Marist/DCC colleges, Walkway over Hudson, Culinary Institute, Vassar Hospital, Hyde Park, New Paltz, Rhinebeck. Couch only in LR would be ok for a child. Pets considered for $15/night fee w/inquiry prior. No full kitchen.

Guest favourite

Cottage in New Milford

4.95 out of 5 average rating, 206 reviews

The Cottage on Babbling Brook

A cozy, rustic cottage beautifully overlooking Wimsink Brook. Custom designed & handcrafted woodwork throughout the home. An all around great spot for families and friends. A magical, peaceful and relaxing space. Conveniently located on the Connecticut/New York border, just a 1 ½ hour drive or metro north from NYC. The area is a prime location, as it offers some of the most stunning and scenic hikes & drives in the country. Only a 10 minute drive from Kent, New Milford or Pawling.

Top guest favourite

Treehouse in Wallkill

4.99 out of 5 average rating, 328 reviews

The Treecastle at the Roundhouse Homestead

The Treecastle started as a vision when I was a child, but came to life during the quarantine of 2020. Escaping into the woods and surrounded by nature, the treecastle is supported on one end completely by a mature pin oak with hardware from Treehouse Masters TV show. Attention to detail shows in this romantic stay that will surely be a memory to last a lifetime. For more photos and videos check out our social media pages : treehouseandchill

Guest favourite

Farm stay in Lagrangeville

4.86 out of 5 average rating, 111 reviews

The Farmhouse

The Farmhouse is a carefully restored home built in 1828. The property has a 4 generation history in the Ryan family. The ultimate retreat for any family, or just a couple that wants a private country estate setting. The home has modern amenities with a true rustic original feel and a view from every window. There have been many memories created on the property and we hope there will be many more for the travelers coming to the Hudson Valley.

Guest favourite

Cottage in Pawling

4.98 out of 5 average rating, 130 reviews

Twin Lakes Designer A-frame Stone Cottage

*Twin Lakes Cottage* Stunningly restored 1930s a-frame stone cottage located on a private lake in West Mountain State Forest with a new deck, patio, soaring high skylights, and 21’ tall wood-burning fireplace. Resting on a hillside with 180 degree views of two lakes, this breathtaking retreat is a one-of-a-kind experience. Surrounded by mature oaks, ferns, and the soothing songs of birds, this remarkable home offers unmatched tranquility.

Guest favourite

Tiny home in Hopewell Junction

4.95 out of 5 average rating, 530 reviews

The GlassHouse: Hudson Valley Tiny Home w/Firepit

The GlassHouse is the much talked-about experience that we had crafted within a sprawling forest preserve. Its wrap-around windows allow breathtaking views to bring out the romantic in all of us! We are stone’s throw up against the Appalachian Trail right on the Dutchess/Putnam line and are less than an hour from Manhattan. Minutes from Fahnestock & Hudson Highlands State Parks & the Empire State Trail!

Top guest favourite

Guest suite in Marlboro Township

4.96 out of 5 average rating, 192 reviews

Viridian House

This space offers a romantic getaway for couples looking to enjoy the scenic Hudson Valley. If you are traveling solo, this cozy space is a private oasis for relaxation and leisure. Centered in the heart of Marlboro wine country, this space is right in the middle of several local wineries, breweries, farms, restaurants, and is just a short drive to the Shawangunk Mountains.