Holiday rentals with a fireplace 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.

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.

(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.

Contemporary Hudson Valley home

Our home is a 1970s architectural gem located in the convenient upstate NY town of Staatsburg. It has been thoughtfully modernized and designed to encourage maximum serenity and enjoyment of both the indoor and outdoor spaces. The floating staircase, huge picture windows, expansive deck and wooded outdoor space make this home perfect for an upstate getaway - while still being close to some of the major area attractions and towns. Our historic street also features 1700s homes and a farm/brewery.

Ridgetop 2 Br Cabin- Views, 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, comfortable bedrooms & quiet workspaces- learn more at cascadafarm.com

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.

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!

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.

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.

The Ancram A - Luxury Mid-Century Modern Cabin

Included in Curbed’s ‘Top 100 Airbnb’s around NYC’! Nestled between the Berkshires and the rolling farmlands of the Hudson Valley, The Ancram A is perfectly situated for your Upstate getaway. This unique A-Frame was originally built in the 60s and then reimagined in 2012 with modern luxuries. The cabin is on a lake so grab a towel and head down for a swim. We look forward to sharing our picturesque hamlet of Upstate NY with you.

Architectural wonder in the woods

Unique experience, secluded. Enjoy a weekend or a few days eco-friendly retreat in an architectural, geometric masterpiece on 30 preserved acres just minutes from all that Rhinebeck and the Hudson Valley have to offer. The house is an open plan, and though it has zero bedrooms, it can sleep 4! Feel free to send us a message for any requests, we love hearing from people.