Vacation rentals in Dutchess County

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Top-rated vacation rentals in Dutchess County

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favourite

Camper/RV in Kingston

4.97 out of 5 average rating, 98 reviews

Glamping Getaway

Come enjoy the sounds of nature when you stay in this unique little getaway. Quaintly tucked away on beautifully manicured private property. Rest, relax & rejuvenate! Conveniently located near the Hudson River & Charles Rider boat launch 1/4 mile to enjoy fishing, kayaking or boating. Walking, hiking, biking trails & kayaking and restaurants located within minutes from the campsite. 5min drive to downtown Kingston, 10min to Historic uptown Kingston. 10min to Saugerties, Woodstock and Rhinebeck.

Superhost

Apartment in Saugerties

5 out of 5 average rating, 3 reviews

Esopus Creekfront I Family I Fire Pit I Kayaks

Welcome to Upstate Waterfronts! Whether you're traveling for the Holidays, visiting family, or looking for a restorative Upstate getaway - this Creekside gem has you covered. - 3 bedrooms/ 1 full bathroom - Fully equipped kitchen & high-end amenities - Private creek access - including kayaks/vests/paddles - Stunning creek views - including a water facing balcony - 3,000 Arcade games, 75'' Smart TV, endless board games - High-speed WiFi - Prime location - walkable to town/restaurants/shops/beach

Superhost

Home in Poughkeepsie

4.76 out of 5 average rating, 123 reviews

Newly Renovated & Comfortable Home-Vassar/Marist

Leave the busy city and the hustle and bustle behind. Relax and rejuvenate yourself in the Hudson Valley. This retreat has all the amenities (fully equipped kitchen, spacious deck/backyard, fire pit, grill, and parking on premises available). Take a walk or bike ride at the Hudson Valley Rail Trail, hike at Mt. Beacon, explore Dutchess Wine Trail c/o Clinton Vineyards, shop at the Poughkeepsie Galleria, or relax at Hand and Stone Massage. There is so much for you, family and friends to do.

Guest favourite

Home in Lake Katrine

4.95 out of 5 average rating, 110 reviews

Waterfront 3BR Home in Hudson Valley, Catskills

Key Residence Features at a glance; Waterfront on the Esopus Creek, Seasonal Kayaks, Rowboat, Dock (approx. Memorial Day weekend-mid October) large yard. Fully equipped kitchen, cable, wireless internet, washer and dryer. Enclosed porch, deck and patio with propane grill and patio furniture. Paved flat driveway, ramp allowing access to first floor, oversize door to first floor bathroom. Three spacious bedrooms with air conditioners. Convenient location close to thruway exits. No boat launch.

Guest favourite

Cottage in Rhinebeck

4.99 out of 5 average rating, 143 reviews

Fabulous Lemon Cottage in Rhinebeck, NY

This cozy, clean, and light-filled cottage with its bedroom loft provides a perfect getaway anytime of the year. When you do venture out, you're in the heart of it all; only a few miles from Rhinebeck village, but also close to Red Hook, Bard, Kingston, Woodstock, Hudson, etc. Use our guidebook to explore the area, or choose to stay in at this quiet, private cottage with views of the woods. LGBTQIA+ friendly. All people from all cultures and backgrounds, without exception, are welcome.

Superhost

Cabin in Rhinebeck

4.89 out of 5 average rating, 356 reviews

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

Guest favourite

Farm stay in Kent

4.88 out of 5 average rating, 301 reviews

(°) The Wandering Peacock (°)

The Wandering Peacock is a unique lodging experience. Outdoor spa, with a cedar hot tub and views of the Appalachian Trail, wood-burning sauna with herbs from the garden. The house showcases vintage machinery, a library, an outdoor kitchen with a pizza oven, and much more. Nestled within the forest foothills of the Appalachia trails, this converted barn is minutes away from downtown Kent and just walking distance from Bulls Bridge, the local river, and waterfalls.

Guest favourite

Home in Pine Plains

4.98 out of 5 average rating, 122 reviews

Twin Island Lake House • Hot Tub

Hudson Valley’s best kept secret. Built in 2018, perched on 4 acres. 3 bedrooms 2 full baths include master suite with private bathroom. Open concept kitchen/living room. A perfect getaway to relax and recharge in our year round 6 person hot tub. Amazing views and sunsets over the lake and mountains. Great hiking, fishing, kayaking, canoeing and bird watching. 16 miles to the center of Rhinebeck. Explore the local farms, restaurants, distilleries and wineries.

Guest favourite

Guest suite in Millerton

4.93 out of 5 average rating, 357 reviews

Romantic Sunset-50 mile view of SNOW

ROMANTIC LUXURY! Winter is in full swing. Cold snowy weather; fresh, crisp mountain air. Clear starry nights. Your own private suite, entrance, kitchen, bathroom, outdoor dining facilities, bar b q grill. Located atop a mountain with magnificent SUNSET view 50 miles overlooking the Hudson River Valley. Completely steam cleaned, disinfected and sterilized before each guest. HEPA Air filters installed. High speed WIFI, 500mbps! 55” 4K HD TV.

Guest favourite

Cottage in Pawling

4.98 out of 5 average rating, 111 reviews

Twin Lakes Designer A-frame Stone Cottage

*Twin Lakes Cottage* Stunningly restored 1930s a-frame stone cottage located on a private lake in West Mountain State Forest with a new deck, patio, soaring high skylights, and 21’ tall wood-burning fireplace. Resting on a hillside with 180 degree views of two lakes, this breathtaking retreat is a one-of-a-kind experience. Surrounded by mature oaks, ferns, and the soothing songs of birds, this remarkable home offers unmatched tranquility.

Superhost

Cottage in Red Hook

4.9 out of 5 average rating, 205 reviews

LAKE COTTAGE WITH HOT TUB - PAINTED TURTLE

Get away from it all to your little slice of paradise. Kayak, swim and rest. Just a hop skip and jump from the city. A blue stone pathways leads to your own private charming cottage overlooking a beautiful spring fed lake with your own private Hot Tub OPEN ALL YEAR ROUND and lake front oasis. Completely surrounded by perennials, and native trees. Lake dock, Hammock and kayaks await you.

Guest favourite

Cottage in Staatsburg

4.9 out of 5 average rating, 189 reviews

Charming Creek side Getaway 3.5 mi. from Omega

Nestled in a creek side hollow, this private and cozy cottage offers a welcoming space to relax and refresh in. The house has a charm all its own, featuring beautiful furnished rooms with the accent on comfortable. Combine that with the creek side setting without another visible house from the property and it truly feels like a "nature's getaway".