Vacation rentals in Union Vale

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Top-rated vacation rentals in Union Vale

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

A sunlit enclosed sunroom features a curved sectional sofa adorned with decorative pillows and a central wooden table. Large windows invite natural light, offering views of the backyard. A rocking chair and potted plant add a cozy touch to the inviting space.

Home in Dover Plains

Hillside Grove

Country hillside retreat. Expansive outdoor patio area complete with Blackstone grill and hot tub. A cozy deck with casual seating nestled amongst the trees and an exquisite natural stone fire pit with six adirondack chairs. An enclosed sunroom overlooking expansive property and sunset. A large harvest table with seating for 8 in the main dining area for more formal gatherings. Fully equipped, recently renovated kitchen and a sitting room for enjoying morning coffee or tea. Large family room.

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4.96 out of 5 average rating, 105 reviews

Top guest favorite

The spacious living area features warm wood paneling and a floor-to-ceiling stone fireplace. Large windows allow natural light to fill the room, offering views of the surrounding greenery. A cozy seating arrangement includes a sectional sofa and armchairs, inviting relaxation.

Chalet in Poughquag

The Lookout

Massive 4,000 sq foot chalet on more than seven acres. Only 90 minutes from NYC, with incredible mountain views and stunning sunsets. Floor-to-ceiling stone fireplace, outdoor firepit, 8 person hot tub, and gas grill for use. Private hiking trail on property. Close proximity to all of Hudson Valley's best golf courses, breweries, wineries, hiking trails, parks, and ski resorts. Easy drive to historic Beacon, Cold Spring, Rhinebeck, Pawling, and New Paltz, and only minutes away from Metro North.

LocationFamilyOutdoor spaces

4.98 out of 5 average rating, 87 reviews

Top guest favorite

A well-maintained exterior view showcases a single-story house with a gray siding. A small patio area features a wooden picnic table surrounded by flower beds and a stone pathway. Lush greenery frames the space, while a clear blue sky fills the backdrop.

Apartment in Verbank

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.

FamilyValueAir conditioning

4.97 out of 5 average rating, 185 reviews

Guest favorite

Guest suite in Lagrangeville

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.

LocationFamilySkiing

4.86 out of 5 average rating, 159 reviews

Top guest favorite

Apartment in Holmes

Top Side

Welcome to Top Side! Nestled in Holmes, NY, Top Side offers lovely views of Whaley Lake. Whether you're looking for a relaxing getaway or an adventure, you'll find plenty of reasons to fall in love with this spacious apartment which is designed to help you unwind and recharge. The Hudson Valley is brimming with activities and attractions for everyone. From historic landmarks and charming villages to outdoor adventures and local dining, you're never far from something special to experience.

FamilyLocationBiking

5.0 out of 5 average rating, 150 reviews

Top guest favorite

The exterior of Millstone Manor is framed by lush greenery and mature trees. The home is characterized by a blend of siding and stone accents, featuring multiple windows and a welcoming entryway. A decorative gazebo with floral arrangements complements the inviting landscape.

Home in Dover Plains

Millstone Manor with East Mountain View

Millstone Manor rests in the eastern Hudson Valley between New York and NW Connecticut--an ideal location to work and play. The driveway leads to the three-bedroom, central-air home with a French-door enclosed library/office. A curated selection of artwork hangs on the walls. Wi-Fi and hardwired Ethernet connections provide internet access to three desks throughout the home. The deck view is a panorama of East Mountain, and the yard is forested with 100-ft-tall spruce and hemlock trees.

LocationFamilyHiking

5.0 out of 5 average rating, 92 reviews

Guest favorite

A rustic cottage is nestled among tall trees, overlooking a flowing brook. A wooden bench sits on a grassy area, with large boulders nearby. The house features a deck and is surrounded by greenery, with a gravel driveway leading up to the front.

Cottage in New Milford

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.

FamilyLocationOutdoor spaces

4.95 out of 5 average rating, 256 reviews

Guest favorite

A pool table occupies the center of the room, with colorful balls scattered across the green felt. A cue stick rests on the edge of the table. Sunlight filters through nearby windows, illuminating the plants and decorative elements surrounding the space.

Home in Pleasant Valley

Welcome to our Stunning Home in the Hudson Valley! Nestled on 7,5 acres, this home is the perfect place to unwind. Featuring 5 spacious bedrooms and 2,5 bathrooms, a pool room and even a gym! Vaulted ceilings, 2 fireplaces, expansive decking overlooks private yard with views. Lovely Gazebo, great for entertaining and perfect for all seasons The beautiful Hudson Valley offers vineyards, parks, walking trails/Rail Trail, antique shops, cozy cafes and Culinary grade restaurants.

FamilyLocationOutdoor spaces

4.93 out of 5 average rating, 28 reviews

Guest favorite

The exterior of the house is framed by lush greenery, featuring a covered porch and a picnic table shaded by a red umbrella. A chiminea is positioned nearby, creating an inviting outdoor space. The gray siding complements the natural surroundings.

Apartment in Dover Plains

*The Ridge House*

Escape to a quiet, pleasant and serene getaway at The Ridge House. A lovely attached apartment with private entrance and covered deck to enjoy the sights and sounds of nature. Stop by the stream down the hill with a drink or enjoy the sunrise while reading outside. Roast marshmallows in the fire after dinner on the grill and finish the day relaxing in the comfortable queen bed. (Airbnb now hides their fees in the listing price, the host cannot change them).

ValueFamilyPets

4.95 out of 5 average rating, 177 reviews

Top guest favorite

A rustic cabin is nestled among tall trees, showcasing a stone chimney and wooden exterior. Warm-colored windows invite natural light, while a gravel path leads to the entrance. Surrounding lush greenery enhances the cabin's secluded setting.

Cabin in Sherman

The Cove Cabin

An original Candlewood style cabin. The house has been updated to offer all modern comforts. It features a large fireplace in the living room, porch over looking the lake, central heat and air conditioning and a fully equipped cook's kitchen. It is on the northern most part of Candlewood Lake with direct, private water access from the shore or the dock. A foam lily pad, two SUP, and two two-person kayaks are available for use from May 1 to November 1.

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4.96 out of 5 average rating, 463 reviews

Top guest favorite

The restored a-frame stone cottage is nestled among trees, featuring a wooden deck and stone steps leading to the entrance. A propane grill is positioned on the deck, with a tranquil wooded backdrop showcasing the colors of nature.

Cottage in Pawling

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.

ValueLocationHiking

4.99 out of 5 average rating, 191 reviews

Top guest favorite

A warmly colored wooden front door features a large window at the top and is adorned with a seasonal wreath. Two carved bear statues stand on either side, complementing a welcome mat placed at the entrance.

Apartment in Millbrook

Red Tail Ridge

One BR with bath, full kitchen, eating area and living room. Separate entrance and sliding glass door in rear with country views. Located on 12 acre parcel. Close to village of Millbrook (less than 4 miles). We are located in center of Dutchess County. There is great antique shopping, historic sites and some of the finest restaurants and chefs with tastes to suit most everyone. .

LocationFamilyAccuracy

4.94 out of 5 average rating, 248 reviews