House vacation rentals in Dutchess County

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Top-rated house rentals in Dutchess County

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Guest favorite

Home in Beacon

4.99 out of 5 average rating, 117 reviews

NEW! Stylish Home in the Heart of Beacon

This Scandinavian style home in the heart of Beacon is bright, airy and modern with beautifully-restored architectural details. Located on a quaint street in the best part of town just steps away from the Roundhouse and Main Street. Enjoy the brewery, bars, restaurants, shops, galleries, and so much more - all within walking distance. Every piece of furniture and decor was handpicked to provide you the perfect designer-quality getaway, focusing on natural simplicity with contemporary luxuries.

Guest favorite

Home in Hyde Park

4.97 out of 5 average rating, 100 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!

Guest favorite

Home in Millbrook

5 out of 5 average rating, 106 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

Home in Rhinebeck

4.93 out of 5 average rating, 208 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

Home in Rhinebeck

4.98 out of 5 average rating, 144 reviews

Long Pond Cottage, Country Retreat in Rhinebeck

Nestled down a quiet, country road, you’ll find this charming, idyllic retreat. Less than 15 minutes from the village of Rhinebeck, Long Pond Cottage captures the best of the Hudson Valley. This two bedroom, one bathroom Victorian sits on just under an acre of land, offering ample outdoor space to enjoy the warmer months, and is the perfect cozy spot when the weather turns colder. Self check-in at 4pm and check-out 11am. Pet friendly. For more photos check out @longpondcottage on IG.

Guest favorite

Home in Pawling

5 out of 5 average rating, 212 reviews

Hobbit House of Pawling

Cozy, one of a kind hobbit house with hot tub! **No children under 12 **No pets (Due to allergies) The ultimate private getaway. 2 bedrooms each with king size beds. 2 bathrooms each with walk in shower. Queen size pull out sofa bed in living room. 3 patios, bbq grill, 2 hammocks, 2 fire pits, electric fireplace in living room. -Hike the Appalachian Trail! -Visit all the historic Hudson Valley has to offer! **No parties **No smoking ~Ring Quests upon request at time of booking!

Guest favorite

Home in Hyde Park

4.85 out of 5 average rating, 208 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

Home in Kingston

4.97 out of 5 average rating, 265 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

Home in Poughkeepsie

4.96 out of 5 average rating, 205 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!

Guest favorite

Home in Highland

4.92 out of 5 average rating, 168 reviews

The Grove: beautiful two bedroom home

The Grove is a cozy two bedroom house located steps away from the village of Highland. We are also a quick drive to not only the best hiking trails but also apple orchards and wineries. The house is equipped with a fully renovated kitchen, washer/ dryer, fenced in back yard, and two parking space driveway. With original craftsman style trim throughout the house you will love staying in our home. All pets are welcome… please review House Rules section for pet fee.

Guest favorite

Home in Wappingers Falls

4.93 out of 5 average rating, 176 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.

Guest favorite

Home in Rhinebeck

4.97 out of 5 average rating, 148 reviews

Honeybug Snug near Omega Institute!

Welcome to the Honeybug Snug! Now with AIR CONDITIONING : ) The Snug is perfect for a family of 4 or 4 close friends. : ) We still have a little work to do on her and you get to watch her grow. Your comments will be taken to heart, as your comfort is our priority! We live right next door if you need anything : ) We are .9 miles for The World Renowned Omega Institute -Center for Holistic Studies. Less than 15 Minutes to Downtown Rhinebeck.