
Vacation rentals with outdoor seating in Dutchess County
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Top-rated accommodations with outdoor seating in Dutchess County
Guests agree: these accommodations with outdoor seating are highly rated for location, cleanliness, and more.

Hoppy Hill Farm House
Enjoy the simple country life in this historic farmhouse. Watch the sun rise over the breathtaking mountain views from the front porch while sipping a cup of coffee/tea. For the more adventurous, there are lots of Appalachian Trail hiking opportunities, and nature preserves to enjoy. Plenty of quaint towns near-by: Kent, Millbrook, Amenia, Wassaic for great food, coffee shops, antiques, parks, breweries and vineries. Inside, you will feel right at home in this comfortable one bedroom apartment.

Modern Upstate Cabin, near Rhinebeck NY
[ 🏊🏽♂️ Heated pool is open May - October 26, 2025. During the colder months we recommend soaking in our giant freestanding tub, which easily fits two humans.] Welcome to Maitopia - our modern, tiny cabin in the middle of a forest. We offer a fully stocked kitchen, a giant bathtub for two, a floating fireplace for cozy winter moments and a heated pool. Plus, a fenced in yard for your pup to roam! Please note: Because of bad experiences we don’t accept bookings from guests without reviews.

Quiet Studio Apartment in Pawling
For getaways or visiting the area, this peaceful sanctuary awaits your arrival in Pawling. A fresh clean studio apartment with idyllic views of the forest, stone walls, and distant mountains. Awake to the sound of birds and beautiful sites. With a king size bed, kitchenette, desk, Smart TV, WIFI, full bath with walk-in shower. Big sliding glass door to private deck overlooking native landscaping. 1 mile to village for restaurants, bakeries, & night spots. 7 min by taxi to Darryl's House Club.

Private ground floor guest suite in Hudson Valley
Newly renovated private, ground floor guest suite returning for 2025 rentals! Br, full bath, large LR w/big TV/frig/mw/coffee in centrally located area in the heart of Hudson Valley. Walk to Dutchess Rail Trail/Uber accessible/self ck in. Close to Poughkeepsie, Beacon, Vassar/Marist/DCC colleges, Walkway over Hudson, Culinary Institute, Vassar Hospital, Hyde Park, New Paltz, Rhinebeck. Couch only in LR would be ok for a child. Pets considered for $15/night fee w/inquiry prior. No full kitchen.

Spilt Milk Cottage - Hudson Valley, NY
Completely renovated 1BR + den cottage inside a circa 1800's dairy barn. Come stay in a perfect WFH base with easy access to the Metro North train and everything the Hudson Valley has to offer. Master bedroom features a full size massaging and adjustable bed with plenty of storage and an office nook. The den is perfect for cuddling up and watching movies or the queen size foldout works as a 2nd bed. Highspeed internet, and a well equipped kitchen to cook up all those locally sourced goodies!

Spacious Studio in Historic home, near Metro North
1st floor studio apartment in a private home. Located in the historic Mt Carmel/Little Italy section of Poughkeepsie. 5 minute walk to Metro North train station and entrance to the Walkway over the Hudson. Many restaurants, coffee/pastry shops within walking distance. There is off street parking and a lovely yard in back. Convenient to Marist College, Vassar College, the CIA, FDR home , Vanderbilt Mansion, Locust Grove, breweries, Rail trails and Wineries. NO third party booking allowed.

The Cottage on Babbling Brook
A cozy, rustic cottage beautifully overlooking Wimsink Brook. Custom designed & handcrafted woodwork throughout the home. An all around great spot for families and friends. A magical, peaceful and relaxing space. Conveniently located on the Connecticut/New York border, just a 1 ½ hour drive or metro north from NYC. The area is a prime location, as it offers some of the most stunning and scenic hikes & drives in the country. Only a 10 minute drive from Kent, New Milford or Pawling.

Eco Cottage in the Woods
The cottage is light and airy, surrounded by forest. You may see birds and deer from the bedroom or living room. The queen bed is divided from the living room by a bookcase wall. There is a sofa bed in the living room which faces a patio overlooking the woods. We have a 16x36 unheated gunite pool, professionally maintained. The cottage works well for a couple or a couple with children. 2 night minimum required. Pets welcome. Pet owners passing through may stay 1 night.

Pine Plains Cottage
Located just 2 hours north of NYC, our country cottage in bucolic Pine Plains is newly renovated and furnished in a modern yet cozy style, welcoming you to a relaxing retreat! It is located in the heart of Pine Plains, a short walk to the town center. Perfect for 2-4 people. We currently have a 2 night min. stay and 3 night min. for holiday weekends. Contact us directly for week/month/shorter stays and to inquire if we can accommodate your pet or a shorter stay!

Relaxing secluded stay with loving social animals.
Do you love nature, animals, and spa comforts? Then this is the perfect place for you! This is a fully finished, private area ground-floor walk-out, in the basement of the main house. Right outside your front door is 800 acres of hiking trails. You are surrounded by a mature forest, with loving and social goats, geese, ducks, kitty, and pups. To enhance this private retreat there are a hot tub and sauna steps from your door. Just Added mini split AC!

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.

Tranquil Tree-House on the beautiful Hudson River
Take it easy at this unique and tranquil getaway. I look forward to hosting you. 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.
Popular amenities for Dutchess County outdoor seating rentals
House rentals with outdoor seating

Upstate Waterfront Saugerties Retreat-Near HITS

Creekside Cottage

Poughkeepsie 3br home near Vassar college/hospital

Serene Retreat with Outdoor Firepit and Pond Views

The Cozy Cape In Historic Hyde Park

Hyde Parks Hideaway

Large 2-BR apartment in historic waterfront home

Little Red Home in the Village
Apartment rentals with outdoor seating

In the Heart of Kingston

Stylish Private Studio 1 block from Main St Beacon

*The Ridge House*

The Carriage House

Cozy Charming Apartment in Private House ⭐️⭐️⭐️⭐️⭐️

Cozy Hudson Valley Retreat | 1800s Farmhouse

Charming Pet Friendly Getaway w Hot Tub & Fire Pit

Under the walkway near the train in Little Italy
Other vacation rentals with outdoor seating

The Lucky Goat Farm

Cozy Mountainside Suite - Minutes from Beacon

Creek Side Cabin w/ Wood Fired Hot Tub & Fire Pit

Modern/lux suite on Hudson Riverfront w/views!

Sackett & Van Dam Guest House @ Little 9 Farm 1706

Airstream Forest Glamping near Metro North Train

Salvato Mill-designer escape w/ private waterfall

Charming Getaway in Historic Poughkeepsie
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- Hunter Mountain
- Belleayre Mountain Ski Center
- Minnewaska State Park Preserve
- Thunder Ridge Ski Area
- The Kartrite Resort & Indoor Waterpark
- Resorts World Catskills
- Bash Bish Falls State Park
- Kent Falls State Park
- Zoom Flume
- Brotherhood, America's Oldest Winery
- Hudson Highlands State Park
- Walkway Over the Hudson State Historic Park
- Catamount Mountain Ski Resort
- Windham Mountain
- Rockland Lake State Park
- Norman Rockwell Museum
- Taconic State Park
- Sterling Forest State Park
- Mount Peter Ski Area
- Opus 40
- Mount Southington Ski Area
- Mohawk Mountain Ski Area
- Beartown State Forest
- Hunter Mountain Resort
- Things to do Dutchess County
- Nature and outdoors Dutchess County
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