Holiday rentals with a patio in Dutchess County

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Top-rated Holiday Accommodation with Outdoor Verandahs in Dutchess County

Guests agree: These Holiday Homes with Outdoor Verandahs are highly rated for location, cleanliness and more.

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Guest favourite

Apartment in Amenia

4.93 out of 5 average rating, 119 reviews

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.

Top Guest favourite

Home in Staatsburg

4.98 out of 5 average rating, 119 reviews

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

Perfect getaway for friends/families in Upstate NY! The newly renovated, spacious 3 bed/3 bath home with BBQ + firepit is just minutes from Rhinebeck + Hyde Park. 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.

Guest favourite

Home in Hyde Park

4.98 out of 5 average rating, 123 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 favourite

Home in Kingston

4.97 out of 5 average rating, 103 reviews

Large 2-BR apartment in historic waterfront home

This sophisticated, cozy, pet-friendly historic home in Kingston's beautiful, walkable downtown waterfront (Rondout National historic district) is close to restaurants, sidewalk cafes, boutiques, parks, a beach, museums, galleries, and more. It features a beautiful front porch and back deck, fenced-in yard, living room, master bedroom (queen bed), 2nd bedroom with (full-sized bed), and den/study adjacent to the second bedroom. It is the perfect retreat for a couple, friends, or a small family.

Top Guest favourite

Cottage in Clinton Corners

4.95 out of 5 average rating, 229 reviews

(Hudson Valley) Laughing Duck Cottage

Located in the bucolic Hudson Valley, this new, gut-renovated cottage isn't far from many of the area's most loved spots. In the winter you can wander trails and get cozy by our electric fireplace. In the spring you can picnic your way through historic sites and enjoy a glass of local wine on our back deck. In the summer you can ride a horse and cook with seasonal ingredients from local farms. In the fall you can hike through the Hudson Valley's perfect colors and sip hot cider on our back deck.

Guest favourite

Chalet in Carmel Hamlet

4.96 out of 5 average rating, 99 reviews

Secluded Lakefront Chalet-Firepit+Yard Dogfriendly

⸻ Just over an hour from NYC, this serene, dog-friendly lakefront chalet offers 200 feet of private shoreline, fenced yard & sunroom with stunning lake views. Thoughtfully decorated with treasures from our world travels, it blends quiet luxury with modern comfort. Enjoy a king bed, fireplace, record player, TV. Dine by the water, relax in the lakeside swing, spot local fauna, hike the nearby trails & unwind fireside. Romantic, peaceful, beautifully secluded – your perfect summer escape awaits.

Top Guest favourite

Home in Staatsburg

5 out of 5 average rating, 96 reviews

Boulder Tree House

Boulder Tree House 🌲🌲🌲 FRESH AIR • SMOKE FREE • ALLERGY FREE Early Check In & Late Check Out! Boulder Tree House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space. Boulder Tree House is ideal for a couple looking for a exciting, romantic and unique experience. The space can also comfortably accommodate a 3rd person.

Top Guest favourite

Cabin in Red Hook

4.97 out of 5 average rating, 105 reviews

Secluded luxury: modern riverfront fishing cabin

Far from the road, this tranquil and unique modern cabin overlooking state stocked fly fishing and tubing river is under 2 hours from NYC. Sited on a 120 acre property, the towns of Red Hook, Rhinebeck, Hudson and Kingston are all between 10 and 30 mins away. On property hiking and tubing for fun. Our chickens mean you'll have fresh eggs on arrival. Radiant floors, swedish compost toilet, a tesla powerwall and 500 mbps internet make it easy to get away from it all while staying in touch.

Top Guest favourite

Guesthouse in Kingston

4.99 out of 5 average rating, 144 reviews

Chic, Private Cabin with Stunning River Views

Private, fully renovated cabin with high-end finishes and stunning views of the Hudson River. All creature comforts including full kitchen, expansive living room, stylish bathroom and cozy bedroom, along with firepit and large deck to watch the eagles from. Nestled on a wooded corner of the owner's property but completely independent with separate driveway, parking and fenced yard for privacy. Just minutes from shopping/dining in Kingston, as well as world world class hiking and nature.

Guest favourite

Apartment in Kingston

4.97 out of 5 average rating, 124 reviews

Rondout Rendezvous

Enjoy the historic Rondout district of Kingston while relaxing in this beautiful, one-bedroom, one bath unit on the first floor of a brick building from 1900. Historic charm meets modern amenities, with 12' ceilings, in-floor heating, and an open concept kitchen, living and dining area across the street from the Hideaway Marina on the Rondout Creek. Take a relaxing walk along the water to the historic waterfront area on Broadway for dining, shopping or a boat ride on the Hudson River.

Top Guest favourite

Home in Saugerties

4.97 out of 5 average rating, 108 reviews

Waterfront, Dog & Family Friendly, Cozy Cottage

El Girasol, "The Sunflower," a sunny, family and pet friendly cottage on the Esopus Creek in the Catskill Mountains. Our home is fully furnished with global & vintage finds. This charming cottage has 2 beds, spacious living room with a big, comfy sleeper sofa and cozy electric fireplace & fully equipped kitchen combined with a dining room. Creek access, BBQ, fire pit, fenced in backyard, & 2 decks makes our home a great destination for a relaxing getaway with family, friends and pets.

Guest favourite

Cabin in Pine Plains

4.96 out of 5 average rating, 247 reviews

The Upstate A - Modern Luxury in the Hudson Valley

The Upstate A is a 3 bedroom + sleeping loft, 2.5 bathroom A-frame set on a quiet cul-de-sac in the heart of the Hudson Valley. Built in 1968, it was fully renovated in 2020-2021. Staying here you’ll experience a cozy yet modern vibe, immersed in nature but with all the accoutrements of an upscale stay. You'll find great hiking in the summer, skiing in the winter, fresh upstate air year-round and serenity all day and night. See for yourself: check us out on IG @upstate_aframe