Vacation rentals in Beekman

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Top-rated vacation rentals in Beekman

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Guest favorite

A bright bathroom space features a pedestal sink with gold faucet fixtures and a large mirror above. Natural light enters through a window adorned with horizontal blinds, showcasing the elegant white and gray hexagonal tile flooring.

Loft in Gardiner

4.94 out of 5 average rating, 31 reviews

Sweet Suite in Gardiner

Forget your worries in this spacious and serene space. The Sweet Suite is a private 1 bedroom with master bathroom ensuite, a lofty open living area amply equipped and handsomely appointed for your comfort. Gardiner continually amazes from season to season for outdoor enthusiasts; the Sweet Suite is near all--Skydive Ranch, Mohonk Mtn House & Preserve, Minnewaska State Park, Auberge Wild Flower Resort, New Paltz Main Street & Water Street Mkt, Tuthilltown Distillery & Farmers Mkt, & Rail Trail.

Top guest favorite

A wide view of the Hudson River features a bridge spanning across the water, connecting lush green hills on either side. The sky is filled with clouds that reflect soft natural light upon the calm surface of the river.

Apartment in Verbank

4.96 out of 5 average rating, 145 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.

Top guest favorite

A spacious area features large sliding glass doors leading to a private deck with two chairs. Natural light fills the space, enhancing views of the surrounding forest. Two windows on either side frame the outdoor scenery, creating an inviting atmosphere.

Apartment in Pawling

5 out of 5 average rating, 89 reviews

Quiet Studio Apartment in Pawling

For getaways or visiting the area, this peaceful sanctuary awaits your arrival in Pawling. A fresh clean studio apartment with idyllic views of the forest, stone walls, and distant mountains. Awake to the sound of birds and beautiful sites. With a king size bed, kitchenette, desk, Smart TV, WIFI, full bath with walk-in shower. Big sliding glass door to private deck overlooking native landscaping. 1 mile to village for restaurants, bakeries, & night spots. 7 min by taxi to Darryl's House Club.

Superhost

The exterior of the Collins Estate showcases a classic white facade with black shutters. A covered porch offers a welcoming entry, surrounded by lush green grass and mature trees. The property features varied architectural details, emphasizing its historic charm and well-maintained grounds.

Guest suite in Lagrangeville

4.86 out of 5 average rating, 148 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.

Superhost

The exterior of a dark blue barn cottage is displayed, featuring a pink door and several small windows. A seating area with bright red chairs is positioned on a leaf-covered lawn, surrounded by trees and greenery.

Guesthouse in Dover Plains

4.87 out of 5 average rating, 116 reviews

Spilt Milk Cottage - Hudson Valley, NY

Completely renovated 1BR + den cottage inside a circa 1800's dairy barn. Come stay in a perfect WFH base with easy access to the Metro North train and everything the Hudson Valley has to offer. Master bedroom features a full size massaging and adjustable bed with plenty of storage and an office nook. The den is perfect for cuddling up and watching movies or the queen size foldout works as a 2nd bed. Highspeed internet, and a well equipped kitchen to cook up all those locally sourced goodies!

Superhost

A classic white fireplace with ornate detailing is highlighted in the foreground. In the background, a doorway leads to a bright, white space, suggesting a clean and modern bathroom area. A decorative rug adds warmth beneath the fireplace.

Apartment in Newburgh

4.86 out of 5 average rating, 191 reviews

Special Nest w Private Entrance River View Porches

Front and back porch, river views, spacious living areas, new & fresh kitchen, and *two* bathrooms make this apartment the ultimate landing spot for a fun vaycay! Located on a street filled with intricate historical homes, this first floor apartment offers an accessible and comfortable getaway. A large backyard is shared with other guests, and sweeping river views are only steps away from your front door. Private entrance, plus easy parking and an electric car charger if you need it!

Guest favorite

A handcrafted wooden staircase features unique railing posts made from natural branches. The rustic feel is enhanced by warm wood paneling that surrounds the staircase. A window allows natural light to filter in, illuminating the organic textures and shapes of the wood.

Cottage in New Milford

4.95 out of 5 average rating, 204 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.

Guest favorite

An outdoor deck is illuminated by warm string lights, creating a welcoming atmosphere. Comfortable seating arrangements include a table and chairs, with a grill visible in the background. The surrounding greenery adds to the serene setting, enhancing the peaceful ambiance of the home.

Cabin in Pleasant Valley

5 out of 5 average rating, 50 reviews

Secluded Mountaintop Getaway

Featured in the Hudson Valley Style Magazine, this Modern Rustic Mountain Getaway is a unique option for accommodations when exploring the Hudson Valley/Taconic region. The secluded getaway is nestled on top of a steep hill and offers stunning views of the surrounding area. Kick back and relax in this calm, stylish space with an amazing outdoor deck or use it as a basecamp for exploring local hiking trails, wineries, distilleries, restaurants, and farms.

Top guest favorite

A wooden serving tray displays a loaf of freshly baked bread alongside a bunch of bananas. A cup is partially visible, suggesting a beverage, while eggs rest in a pink bowl nearby. The table is made of natural wood, showcasing its unique grain patterns.

Treehouse in Wallkill

4.99 out of 5 average rating, 317 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 favorite

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 favorite

The exterior of the stone cottage is framed by lush autumn foliage. A spacious wooden deck features several lounge chairs, providing a relaxing outdoor space. The entrance is marked by a subtle stone pathway, enhancing the inviting appeal of the cottage.

Cottage in Pawling

4.98 out of 5 average rating, 126 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.

Superhost

A countertop arrangement includes a decorative canister with a black lid and a mosaic design, paired with a potted rosemary plant in a blue and white pot. A small white alarm clock is positioned in front, displaying the time.

Guesthouse in Stormville

4.97 out of 5 average rating, 175 reviews

Hudson Valley Cottage with Pond Access

Light and airy cottage situated on the private eighteen acre property surrounded by beautiful mature trees, large lawn area and quick two minute walk to a beautiful large 3 acre pond. Perfect spot for a relaxing weekend in the Hudson Valley; only 60 miles from Manhattan. The cottage has it's own private back yard, with a patio and a fire pit. Perfect place to disconnect and relax. Enjoy your Hudson Valley getaway!