Vacation rentals in Shorehaven

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Top-rated vacation rentals in Shorehaven

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Guest favorite

Guest suite in Dover Plains

4.91 out of 5 average rating, 314 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 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, 90 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

A wooden deck is surrounded by lush greenery, featuring two lounge chairs positioned for relaxation. A charming cabin stands in the background, accentuated by a mix of trees and plants that create a secluded atmosphere.

Cottage in Carmel Hamlet

4.84 out of 5 average rating, 164 reviews

Lake Cabin Escape–Fenced Yard+Firepit.Dogs welcome

⸻ A cozy, art-filled cabin just over an hour from NYC, steps from a swimmable lake. Decorated with unique treasures collected from around the world, it’s a soulful space made for rest & reconnection. Enjoy a stone fireplace, fenced yard for pups, starry nights by the fire pit & peaceful mornings on the deck. Hike nearby trails & slow down. This isn’t just a cabin — it’s a story-filled retreat designed to help you rest, relax and rediscover what matters. Come for the lake. Stay for the magic!

Top guest favorite

A deer stands among lush greenery, closely watched by a fawn that is nursing. The scene captures the gentle presence of wildlife among the natural surroundings, with soft grass and a dense backdrop of leaves and branches.

Home in Holmes

5 out of 5 average rating, 40 reviews

A Seclusive Retreat by the Water at Hudson Valley

Let yourself unwind in our secluded, peaceful 22-acre Zen paradise. Stay in a newly remodeled guest house with all new modern amenities and views of your private 2-acre pond and lush landscape from every room. Sip your coffee by the pond, stroll the surrounding hiking paths, say hello to the blue heron, turkeys or deer that may cross your way, relax and breath in the fresh air. Even though it may seem far from civilization, it is surprisingly only 60 miles north of NYC, in Hudson Valley.

Top guest favorite

A wooden deck features a single reclining chair positioned on a patterned area rug. The space is surrounded by a wooden railing, providing views of the tranquil lake and lush greenery in the distance.

Cottage in Holmes

5 out of 5 average rating, 22 reviews

The Whaley Lakeside

Unwind at our newly renovated two-story lakefront getaway nestled on the shores of beautiful Whaley Lake. Just 80 minutes from NYC, it's the ideal weekend escape for families, couples, and friends—dogs included! Spend summer days kayaking, swimming, or dipping your toes off your private dock. Two spacious decks provide the perfect setting for morning coffee, evening cocktails, or just soaking in the peaceful lake views. And our new generator means everything works even in stormy weather!

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, 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.

Guest favorite

Chalet in Holmes

4.95 out of 5 average rating, 40 reviews

Hudson Valley Lakeview Retreat - Lake Access

Relax and enjoy nature in this lakeside retreat! Only 75 minutes from Manhattan, with Metro North access nearby. Wake up to the sunrise over the lake with stunning views from the master bedroom; enjoy the private lake or one of many nearby hiking & biking trails; cook in the fully equipped kitchen or outdoor grill; and wind down with a bath in the jetted tub and a fire in the indoor wood stove or outdoor fire pit. UPDATE: Summer Lake view is back! Freshly trimmed trees and bushes.

Top guest favorite

A wooden dock leads up to the hillside cabin, bordered by lush greenery. Two paddleboards are securely positioned on the dock, alongside white Adirondack chairs. A fire pit sits on the dock, enhancing the lakeside retreat's inviting ambiance.

Cabin in Holmes

4.97 out of 5 average rating, 36 reviews

A View From the Lakehouse

Welcome to paradise! Come meet your family’s new favorite vacation home, where your backyard is Dutchess County's largest private motorboat lake and your commute is less than 90 minutes from Manhattan. Lounge in the sun on our private dock, explore all the lake has to offer on our state of the art fiberglass paddleboards, and take in the stunning views from this beautifully renovated cabin, tucked away on a hillside amongst the lush foliage. Come enjoy lakeside living at its finest!

Top guest favorite

A treehouse structure is observed elevated among lush greenery, supported by a prominent tree. The exterior features dark siding, a distinct gable roof, and vibrant orange doors. A spiral staircase leads to the entrance, while a natural clearing surrounds the base.

Treehouse in Wallkill

4.99 out of 5 average rating, 320 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!