Holiday rentals in Pleasant Valley

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Top-rated holiday rentals in Pleasant Valley

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Top guest favourite

Loft in Pleasant Valley

5 out of 5 average rating, 44 reviews

Be our guest at The Nest!

Your Hudson Valley hideaway awaits at “The Nest”! Located only minutes from the Taconic, a short drive to Millbrook, Rhinebeck, & historic Hyde Park. 8 minutes to Baird Golf course. Conveniently located only about 20 mins from Vassar College, Marist, the Culinary Institute, Walkway Over the Hudson, & Barton Orchards. 30 minutes to Red Hook & Beacon. The property offers beautiful trees & plenty of privacy. It’s a perfect retreat to get away and enjoy all that the scenic Hudson Valley has to offer

Guest favourite

Home in Pleasant Valley

5 out of 5 average rating, 30 reviews

The Wildflower House

Welcome to The Wildflower House, a serene modern retreat nestled in the heart of the Hudson Valley. Just 90 minutes from NYC by car & 15 minutes from Metro-North, it’s the perfect base for exploring Dutchess County and beyond. Enjoy easy access to charming towns like Millbrook (10 min), Rhinebeck (20 min), and Kingston (30 min), plus excellent hiking, dining, and antiquing—all minutes from your door. Great for a cozy weekend getaway or longer retreat to relax or focus on your next big project.

Top guest favourite

Flat in Verbank

4.96 out of 5 average rating, 146 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 favourite

Apartment in Poughkeepsie

4.97 out of 5 average rating, 309 reviews

Spacious and stylish entire one bedroom apartment.

Enjoy a stylish experience at this centrally-located one bedroom apartment in Poughkeepsie. Apt is located in a quiet Victorian townhouse on the 3rd floor. Entire rental unit, Parking is included for one vehicle. Located downtown. Walking distance to: Post Office, Courts, County Bldgs, Police Station, City Hall, Nesheiwat Convention Center (fka Civic Center), Poughkeepsie Grand Hotel, Walkway Over The Hudson, Bardavon Opera House, The Academy, train station, waterfront, bus depot, and more.

Guest favourite

Home in Hyde Park

4.85 out of 5 average rating, 218 reviews

Village Cape Getaway

Village Cape on Albany Post Rd in the historic town of Hyde Park. Surrounded by gardens, stone walls, private parking/entry. This 2 story house offers a 1 bdrm apartment that sleeps 3 on the 2nd floor. Close to markets, shops, restaurants. 1 mi to Vanderbilt Mansion, FDR house and library. 2mi to the Culinary Institute of America. 4mi to Marist College. Hiking trails walking distance. Historic drive-in movie in town. Metro north Poughkeepsie sta 6mi south offering taxi and bus service.

Superhost

Tiny home in Poughkeepsie

4.86 out of 5 average rating, 122 reviews

Lake Side Tiny House

Reconnect with nature at this unforgettable escape. Sitting on a beautiful 5 acre property, tucked back in the woods along a beautiful lake. Come stay and unwind. Plenty to explore and just be. Lake access for swimming or with paddle board, canoe, or kayak. Just ask and can be assisted with. The whole property has been curated to be a playground. Full bathroom inside unit. Brand new Mini Split heat and AC unit. Works amazing Has most kitchen amenities besides an oven. Enjoy

Top guest favourite

Guest suite in Poughkeepsie

4.96 out of 5 average rating, 127 reviews

Suite of Rooms in Historic Home

Wonderfully decorated 3rd floor suite of rooms in the Academy Historic District. Two Newly renovated bedrooms, one with queen bed, the other with 2 twin beds. There is an additional day bed in the living area/ sitting room space , a TV with Netflix & Amazon Prime with wifi connection throughout. The bathroom has modern fixtures and a claw-foot tub/shower. There is a private entrance with additional half bath . A private porch and use of the beautiful backyard.

Guest favourite

Cabin in Pleasant Valley

5 out of 5 average rating, 51 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 favourite

Treehouse in Wallkill

4.99 out of 5 average rating, 322 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

Home in Hyde Park

4.89 out of 5 average rating, 530 reviews

Cozy ranch near FDR Historical Site

My warm & inviting ranch home has a true homey feeling. It comfortably accommodate 4 people (please unreported guest will be charged extra $15 per person per night just be honest about it); located in heart of Hyde Park. Just mins to Culinary Institute of America and Marist College; perfect for parents attending graduations or orientations , FDR Presidential Library, Vanderbilt Mansion and Walkway over the Hudson all within mins away.

Guest favourite

Flat in Millbrook

4.93 out of 5 average rating, 230 reviews

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. .