Pleasant Valley places to stay

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Top-rated places to stay in Pleasant Valley

Guests agree: these places to stay are highly rated for location, cleanliness, and more.

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Guest favorite

Apartment in Staatsburg

5.0 out of 5 average rating, 190 reviews

Through the Woods Farm

Through the Woods Farm is our 23-acre home. Located in northern Dutchess County; we're minutes from Omega, and the villages of Rhinebeck, Red Hook, Millbrook, and Hyde Park. The apartment is ideal for a single guest or a couple; maximum allowed is 4 adults. Each additional adult over 2 adds $50/per night. The second bedroom is small - two adults in it is a tight fit! If you're looking for a peaceful, rural getaway in an immaculate, private apartment that's close to everything, you've found it!

Oct 27 – Nov 3

G$30,595 GYD per night

Guest favorite

Home in Salt Point

4.95 out of 5 average rating, 134 reviews

The Literary Inn-entire house

This 3 bedroom guest house located in Salt Point, Dutchess County in New York State. This quiet private place on a 4 acre property is less than 10 minutes from the Taconic Parkway. The house has cable TV, free wifi, central air and heat, a full kitchen with a dishwasher, a full bathroom, a large deck and private patio. The Hudson Valley is home to Colleges, Museums, historic towns, and great State Parks. There are restaurants offering vegetarian and vegan dishes and super markets are nearby.

Jul 12 – 19

G$43,044 GYD per night

Guest favorite

Apartment in Lagrangeville

5.0 out of 5 average rating, 130 reviews

Country Oasis | Centrally Located | Strong WiFi

Stay in this serene 2 bedroom apt. right in the heart of the Hudson Valley! Conveniently located only 20 minutes away from Vassar, Marist and the Walkway Over the Hudson! Includes private parking, strong WiFi and a fully equipped kitchen. Enjoy all the greenery from your private deck. Sleep on comfortable queen size beds in each bedroom. Unwind in the living room watching your favorite movies on Netflix. Make this country oasis your home base as you explore all the wonders of the Hudson Valley!

Oct 4 – 11

G$42,817 GYD per night

Guest favorite

Condo in Poughkeepsie

4.97 out of 5 average rating, 224 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.

Jul 12 – 19

G$28,916 GYD per night

Guest favorite

Cottage in Highland

4.91 out of 5 average rating, 542 reviews

Little Yellow Cottage New Paltz - Kitchen wash/dry

Built over 100 years ago as a chicken hatchery, this gorgeous little gem has been fully restored as a two-story guest cottage. Located in New Paltz just minutes off Exit 18 on I-87 in a very private, quiet, country setting. Only ten minutes from New Paltz Village & SUNY New Paltz and set back on a lightly traveled road for those long summer strolls. You don't even need a car to get here! It's just 12 minutes by taxi from the New Paltz Bus Station or bring your bike up and cycle everywhere!

Sep 9 – 16

G$32,526 GYD per night

Guest favorite

Home in Hyde Park

4.85 out of 5 average rating, 184 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.

Aug 14 – 21

G$21,231 GYD per night

Guest favorite

Apartment in Lloyd

4.99 out of 5 average rating, 102 reviews

Cozy & Tucked Away - 1 Bedroom Apartment

A tiny, one bedroom apartment with a private entrance located on the upper level of a newly renovated 100 year old farmhouse. Centrally located between New Paltz and Poughkeepsie, and only minutes away from The Walkway over the Hudson. The house has a natural rock wall behind it leaving you feeling "tucked away" on our quiet street. Your hosts live in the downstairs apartment, and would love to provide you a comfortable and cozy stay as you explore their home, the Hudson Valley!

Jun 17 – 24

G$23,961 GYD per night

Superhost

Apartment in Salt Point

4.82 out of 5 average rating, 136 reviews

Arcady - Modern, 1br cottage

Renovated 600 sq ft 1br/1ba cottage! Welcome to Arcady - an ideal rustic paradise. Our recently renovated barn cottage situated on 6 acres of land with private creek and within easy drive of Rhinebeck, Millbrook, Omega Institute, Poughkeepsie and thousands of Hudson Valley Attractions. 10 min drive from Omega, 1 min drive from a town beach - enjoy everything area has to offer including hikes, mansions, farm visits, wineries and much more.

Jul 17 – 24

G$28,463 GYD per night

Guest favorite

Apartment in Stanfordville

4.95 out of 5 average rating, 154 reviews

Country Apartment great for a romantic getaway

Second story apartment above garage with private entrance has everything you need for a comfortable getaway. Located on quiet rural neighborhood road with off street parking. Enjoy nature right out your door walking to the beaver pond in the back woods or on the many nearby hiking and biking trails. Relax in the backyard. An easy drive from the Taconic Parkway or 20 minutes from the Metro-North Wassiac train station.

Sep 17 – 24

G$28,556 GYD per night

Guest favorite

Home in New Paltz

4.97 out of 5 average rating, 681 reviews

Victorian Haven

Victorian Haven is located near the Shawangunk Mountains that extends for over 20 miles and reaches 2,200 feet in height at Sam's point, the highest elevation on the ridge. In addition, the Wallkill River provides unspoiled and picturesque spots for hiking, fishing and/or picnics. Gardiner has a beautiful rail trail that follows the path of the 1860's railroad and provides a great opportunity to hike, bike or ski.

Feb 19 – 26

G$27,442 GYD per night

Guest favorite

Apartment in Millbrook

4.93 out of 5 average rating, 206 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. .

Jan 19 – 26

G$26,159 GYD per night

Guest favorite

Apartment in Millbrook

4.98 out of 5 average rating, 280 reviews

Blue Cottage Apartment in Village of Millbrook

This is a private apartment on the second level of the home two blocks from the Village center of Millbrook. The space was newly renovated and includes a separate entrance to the apartment, 2 bedrooms (with AC and Tvs), full bathroom, sitting area, and kitchenette. Perfect for couples, small families or individuals visiting the area. WIFI and cable are provided.

Feb 22 – Mar 1

G$35,347 GYD per night