Places to stay in Pleasant Valley

4.93 out of 5 average rating, 108 reviews

Apartment in Amenia

Amenia Main St Cozy Studio

Cozy studio in well maintained house from 1900. 150 sq ft with full size bed. Unit is comfortable for one, tight for two. Right in small town of Amenia. Front porch with seats/table. Walking to food, shops, drive-in movie theatre, and rail trail. Trail is 1/4 mile from house, paved and only allows walking/biking. On trail: Arts village Wassaic (3 miles south) Millerton (8 miles north). Train to NYC is 2.5m south. Tons in area: wineries, distillery, lakes, hiking, theatre & quaint towns.

4.96 out of 5 average rating, 144 reviews

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.

4.97 out of 5 average rating, 307 reviews

Condo in Poughkeepsie

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.

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!

4.85 out of 5 average rating, 217 reviews

Home in Hyde Park

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.

4.86 out of 5 average rating, 190 reviews

Apartment in Newburgh

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!

Tiny home in Poughkeepsie

4.86 out of 5 average rating, 120 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

4.89 out of 5 average rating, 382 reviews

Cabin in Rhinebeck

Sunset Bungalow-Mt views on 130acre forest & falls

Newly renovated private cabin on the ridge top of an 130 acre magical property with stunning western views and overlooking a historic farm & crystal clear lake. Explore the hiking trails, dip in the wading pools of the upper cascades, bike to town or simply enjoy the peaceful sounds of the 90ft waterfall on the property. Relax in a beautifully designed private retreat, complete with a gourmet kitchen, cozy fireplace, and comfortable bedroom- learn more at cascadafarm.com

4.99 out of 5 average rating, 317 reviews

Treehouse in Wallkill

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

4.89 out of 5 average rating, 528 reviews

Home in Hyde Park

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.

4.93 out of 5 average rating, 230 reviews

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. .

Guest suite in Marlboro Township

4.96 out of 5 average rating, 181 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.

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Other great vacation rentals in Pleasant Valley

Guest suite in Ulster Park

4.94 out of 5 average rating, 117 reviews

Sunny and Spacious Studio - a serene getaway

HanRating, 5 stars3 days ago

This is one of the best, most well-priced AirBnBs I have found for solitary retreats. Everything looks just as presented in the listing. Being there in person was even better than I imagined. There are very high ceilings in this space, and the light is beautiful. The view of the leafy backyard is most peaceful and calming.

4.96 out of 5 average rating, 172 reviews

Home in Rhinebeck

Honeybug Snug near Omega Institute!

ChristinaRating, 5 stars2 weeks ago

we stayed at Garrett's while attending a retreat at Omega. it's a beautiful little home on a gorgeous property. very comfortable and clean, it is a very charming space.

5 out of 5 average rating, 27 reviews

Home in Pleasant Valley

The Wildflower House

MatthewRating, 5 stars1 month ago

Loved every part of our stay with Kristine. Perfect for a romantic weekend away - gorgeous cabin, well appointed, and great kitchen for cooking-in. Her recommendations for local spots were also so thoughtful. Thank you again!

4.85 out of 5 average rating, 177 reviews

Apartment in Salt Point

Arcady - Modern, 1br cottage

ChipRating, 5 stars1 week ago

Great location, close to everything, let very private. Host was very helpful and responsive when assistance was needed. Recommend to other guest.

4.98 out of 5 average rating, 189 reviews

Home in Verbank

The Waterfall House

JessicaRating, 5 stars2 days ago

This place is truly a gem! We enjoyed swimming in the waterfalls and relaxing under the trees. We can’t wait to return. The house is also lovely with lots of interesting and quirky touches that we enjoyed. Incredibly well stocked kitchen and everything we could want!

4.9 out of 5 average rating, 627 reviews

Cottage in Highland

Little Yellow Cottage New Paltz - Kitchen wash/dry

HardyRating, 5 stars2 weeks ago

I usually stay in village of New Paltz so was a little apprehensive staying a bit outside of village. But I actually now prefer the situation as it's not that far to all the action and the cottage is amazing, which more than makes up for the minor driving inconvenience. Highly recommend!!

4.96 out of 5 average rating, 244 reviews

Home in Poughkeepsie

CaitlinRating, 5 stars1 week ago

In town for a friend's wedding and had a lovely stay at Amy & Lloyd's house. Close to where we needed to be, responsive hosts, and easy to find (yellow door!). Enough room for everyone to stretch out and relax. Thank you!