House vacation rentals in Dutchess County

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Top-rated house rentals in Dutchess County

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Guest favorite

The exterior of the Piersaull House is presented, featuring light beige siding and a welcoming porch with a white railing. Lush greenery surrounds the property, including tall trees and shrubs. A wooden bench is situated nearby, enhancing the outdoor space.

Home in Hyde Park

4.97 out of 5 average rating, 110 reviews

Cozy Historic Piersaull House - Charming & Quirky!

Piersaull House, built in 1910 by Charles Piersaull, Hyde Park's fishmonger, photographer, and bicycle repairman, features 630 sqft of quirk and charm, in the heart of the Hudson Valley. This small home lives big with living, dining and kitchen on the first floor, and 2 beds and 1 bath upstairs. Very tall people are destined to bonk their heads in an upstairs room, but will likely grin and relish the charm of this historic property. The privacy of your own house at the price of a hotel room!

Top guest favorite

A modern kitchen features white cabinetry, stainless steel appliances, and a spacious island with seating. Natural light floods the area through a large window, highlighting the light wood flooring and the elegant contrast of dark accents. A green plant adds a touch of nature to the space.

Home in Staatsburg

4.98 out of 5 average rating, 111 reviews

3BR/3BA Renovated Retreat w/ Firepit By Rhinebeck

Perfect weekend getaway for friends or families in Upstate NY! The newly renovated, spacious 3 bed/3 bath home with BBQ + firepit is just minutes from Rhinebeck. Nearby attractions include hiking, breweries, kayaking, restaurants, wineries, historical sites, colleges (Marist, Vassar, Bard), golf, farms, skiing + more. 15 min drive to Metro-North & Amtrak for easy travel to/from NYC. 5 min walk to Mills Norrie State Park. 2 hr drive from NYC. 10 min drive to Rhinebeck. 25 min drive to Kingston.

Top guest favorite

The exterior of a modern wooden house is surrounded by lush greenery. Large windows allow natural light to fill the interior. A neat lawn leads to the entrance, which is framed by manicured bushes and trees in the background.

Home in Millbrook

5 out of 5 average rating, 113 reviews

Stunning Views, Light and Open - The Beech House

Named for one of it's giant beech trees, The Beech House is a modern, sunlit home with gorgeous views of the Catskills. All are welcome to come, relax, and unwind in our warm, open, comfortable home. The Beech House sits on 4 lush acres, off a quiet lane, just an easy walk to the village of Millbrook in Dutchess County. The house is perfect for relaxing or playing, staying in or going out, couples, friends, or families. We absolutely love it and it is our great pleasure to share it with you.

Guest favorite

The exterior of a charming two-story home is surrounded by lush green grass and mature trees that showcase autumn foliage. The house features a welcoming porch and is set against a backdrop of peaceful woods, providing a serene setting for relaxation.

Home in Staatsburg

4.97 out of 5 average rating, 117 reviews

Welcome to Your Hudson Valley Escape

Historic colonial charm meets modern luxury in this peaceful pristine upstate escape, that features 2 private bedrooms and extra sleeping in a finished basement. Just minutes from Rhinebeck Village and walkable to scenic Hudson River trails this home has been crafted with care by preservationist owners. Chef's kitchen Sleeps 4-6 Great room w streaming TV, grand piano, fireplace Antique details + modern upgrades Flower gardens and wooded tranquility Minutes to restaurants, boutiques, shops

Guest favorite

A spacious living area showcases light-colored sofas arranged around a wooden coffee table. Large windows provide views of the lush outdoors, while a patterned rug anchors the space. A chair and stylish lamps enhance the inviting atmosphere.

Home in Staatsburg

4.96 out of 5 average rating, 124 reviews

Light and Spacious Designer Retreat near Rhinebeck

Nestled among the trees, this roomy home is off a quiet road in a historically scenic area (between Rhinebeck and Hyde Park). The house features lots of light, direct pond access , indoor fireplace, and renovated kitchen. We offer a great value while providing high-end amenities like luxury linens and towels, hybrid memory foam beds, and down pillows and comforters. This home sleeps eight (and up to ten with the two rollaway beds) and is the perfect getaway for a group trip or family stay.

Guest favorite

A wooden bridge spans a gently flowing creek, surrounded by vibrant foliage in various autumn hues. The lush, wooded area features scattered rocks and a grassy bank, inviting exploration and relaxation in a serene natural setting.

Home in Rhinebeck

4.93 out of 5 average rating, 230 reviews

3Br Creekside Cottage on 130 acre forest w/ trails

Creekside Cottage is an extraordinary private escape nestled against a winding creek running through the rocky gorge of an 130 acre magical historic farm. Explore miles of hiking trails through old forests, trout creeks, and a 90ft waterfall or simply relax by the fire pit while listening to the flowing water. Visit this beautifully designed retreat, complete with gourmet kitchen, cozy fireplaces, great wifi and comfortable bedrooms with quiet workspaces- learn more on our site cascadafarm

Guest favorite

The front entry of the house is framed by flower pots and flanked by twin windows with dark shutters. A welcome mat lies outside the dark front door, which features a decorative door handle and is set against a pale yellow exterior. An American flag gently sways in the breeze.

Home in Hyde Park

4.85 out of 5 average rating, 217 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.

Guest favorite

A bright bedroom features a large window dressed in sheer white curtains, allowing natural light to fill the space. A view of the outdoors is visible, highlighting trees and a wooden deck beyond the window. A spacious bed with crisp white linens is positioned near the window.

Home in Poughkeepsie

4.93 out of 5 average rating, 358 reviews

Charming home near Walkway Over The HUDSON

Totally renovated home conviently located near by train station, Marist College, Vassar College, Culinary Institute of America, FDR Library, Walkway over the Hudson. My home is a 2 story home built in 1856; it has one bedroom and full bathroom on each floor. We refinsihed 9 inch pine wood floor trying to keep most of yesterday in the house. kitchen is fully equipped with snacks and coffee, tea! SORRY WE DO NOT PROVIDE BREAKFAST WIFI WITH SMART TV ONLY (NO CABLE) 2 parking spaces

Top guest favorite

A welcoming entrance to the home is framed by a red door and a decorative lantern. Lush greenery and vibrant red flowers are visible in planters, contributing to the serene outdoor setting. The backdrop features a brick building with large windows and climbing plants.

Home in Kingston

4.97 out of 5 average rating, 294 reviews

DeMew House in Historic Kingston

PRIVATE, ELEGANT ONE KING BEDROOM HOME! DeMew House is an exclusive renovated 1850s brick home, a block from the historic Kingston waterfront. Enjoy total privacy in an elegant, transitional two-story home with an open floor plan that is inviting, warm and intimate. The home, across from a marina, has a king bedroom, a pull-out sofa bed, an en suite bathroom with two-person shower and double vanity. A full kitchen, ac, private driveway and gazebo frame this discerning getaway...

Guest favorite

A sunlit living room features a spacious gray sofa and a decorative coffee table. A large television is mounted on the wall, displaying a serene sunset. An archway leads to a dining area with white chairs and a dining table, enhancing the open concept design.

Home in Poughkeepsie

4.96 out of 5 average rating, 237 reviews

The whole group will enjoy easy access to everything from this centrally located home. Ample space inside and out for creativity, relaxing and enjoying! Located in a quiet, residential, family-oriented neighborhood. This retreat is less than 1 mile from Marist College, and the Walkway Over the Hudson. A ten-minute drive to The Culinary, Vassar College and all FDR historic sites/attractions. Also, enjoy 125 cable and Roku tv Channels. Make this home your home away from home!

Top guest favorite

A serene view of the Hudson River at sunset, with vibrant colors reflected in the water. A silhouetted tree stands in the foreground, while the sky is adorned with clouds that capture shades of orange and purple, enhancing the tranquil atmosphere of the surroundings.

Home in Wappingers Falls

4.93 out of 5 average rating, 216 reviews

Tranquil Tree-House on the beautiful Hudson River

Take it easy at this unique and tranquil getaway. Be our guest at our beautiful home located on the widest part of the Hudson River. Enjoy a private room with a queen size bed and a large screen smart tv. The full bathroom is located across the hallway. Enjoy a warm fire in the sitting area. There is a work area and a high table to enjoy some tea/coffee or wine with dinner while enjoying the view of the Hudson through the large windows and sliding door.

Superhost

A fully equipped kitchen features modern cabinetry and stainless-steel appliances. A gas stove and built-in microwave are visible, along with a coffee maker. The countertop is complemented by a stylish backsplash in neutral tones. An adjacent dining area provides seating for four.

Home in Hyde Park

4.89 out of 5 average rating, 525 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.