Holiday rentals with outdoor seating in Dutchess County

Slate Cabin - Stylish Country Escape x Rhinebeck

This designer cabin blends natural materials and modern finishes. — sophisticated & cozy. Gaze at (or swim in!) the stunning spring-fed pond steps from the house. Lounge on the deck or enjoy coffee in the sunroom. The interiors feature three bedrooms, two full bathrooms, living room with chic and cozy furniture and wood burning fireplace, and fully appointed kitchen that's a joy to cook in. Entertain your family & friends at the table for 10 and continue out to the grounds, beverage in hand.

Design-Forward Riverfront Cabin on 120 Acres

Far from the road, a tranquil modern cabin sits directly above a state-stocked fly-fishing and tubing river - an intimate, private escape under two hours from NYC. Set on a 120-acre property, with access to trails, river swimming, and a private cabin beach, you’ll feel completely secluded while still being 10–30 minutes from Red Hook, Rhinebeck, Hudson, and Kingston. Radiant floors, a Swedish composting toilet, Tesla Powered, w/ 500 Mbps fiber internet make it easy to unplug without sacrificing.

(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.

Magical Private Island Retreat in Pine Plains

Enjoy the serenity of Twin Island Lake, surrounded by tranquil water, lush mountains and nature. this incredible private island retreat is only 2 hours from NYC. Take a canoe across a lily pad dotted lake to your own private island paradise. You will never find a magical space like this so close! The entire island is yours to enjoy and has plenty of outdoor spaces including a propane grill, hammocks and plenty of seating areas. The inside a humble aesthetic with wood paneling and charm.

Top Side

Welcome to Top Side! Nestled in Holmes, NY, Top Side offers lovely views of Whaley Lake. Whether you're looking for a relaxing getaway or an adventure, you'll find plenty of reasons to fall in love with this spacious apartment which is designed to help you unwind and recharge. The Hudson Valley is brimming with activities and attractions for everyone. From historic landmarks and charming villages to outdoor adventures and local dining, you're never far from something special to experience.

Waterfront Cottage - Hot Tub, Kayaks and Fire Pit

Welcome friends to our beloved waterfront cottage right on the Esopus Creek, in the beautiful Catskills! Whether you’re seeking a peaceful retreat, fun for the family, or a romantic escape, our 2-bedroom home is your perfect Catskills destination. With kayaks for adventures on the creek (Spring through Fall), a firepit with water views, outdoor dining with a grill, and located close to lots hiking and nearby towns, like Woodstock and Saugerties, you'll only wish you could stay here longer!

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.

3Br Hilltop Ranch on 130acre farm w/ falls & creek

Newly renovated ranch house on a private hill top of an 130 acre magical property with stunning eastern views and overlooking a historic farm. Explore the hiking trails, dip in the wading pools of 90ft waterfall's upper cascades, bike to town or simply relax on the hammock while taking in views of the rolling hills. Escape to a beautifully designed private retreat, complete with a gourmet kitchen, cozy fireplaces, and comfortable bedrooms with quiet workspaces- learn more at cascadafarm

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.

Secluded Hilltop Cabin near Beacon & Cold Spring

3 private acres atop small mountain, next to massive forest preserve. 90 min from NYC but feels like you're way upstate. 130+ 5-star reviews! Cozy deck w grill overlooks Mt. Beacon sunsets. Loft w/queen and twin mattresses + twin-size mattress day bed on the porch. Fast WiFi. Fire pit and stacks of cut wood. Plus waterfall area with meditation pier (but waterfall only active Apr-Jun) 5 miles from Beacon restaurants & Cold Spring hiking trails.

Creekside Cottage | The Fitz House Red Hook NY

**NEW 50” TV INCLUDED** Welcome to The Fitz House - a 2 bedroom / 1 bath 1950's cottage located along a peaceful, quiet road in the Hudson Valley - Red Hook, NY. Built alongside a stream and perched upon a ridge, the cottage sits on 6 acres of private land. The Fitz House recently underwent a major renovation in late 2022 and offers all of the comforts of home. We look forward to having you and sharing our little slice of the Hudson Valley!

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.