Cottage vacation rentals in Dutchess County

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Top-rated cottage rentals in Dutchess County

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Guest favorite

A heated pool is surrounded by a stone patio and secured by a metal fence. Lounge chairs line one side of the pool, with a serene wooded backdrop providing privacy. Morning light reflects on the water's surface, creating a calm and inviting atmosphere.

Cottage in Clinton Corners

4.89 out of 5 average rating, 168 reviews

Tranquil Cottage in the Country

Beautiful three bedroom cottage located on a pretty knoll with private access. Heated pool and outdoor living, in a peaceful country setting - with all the tranquil beauty and amenities of the Hudson Valley. Only 1.5 hours from Manhattan and 15 minutes drive to the historic town of Rhinebeck. Great for a weekend getaway. House is perfect for all four seasons; cool in summer and warm in winter. Beautiful decor and suitable for professional people needing an escape from the stress of the city!

Guest favorite

Cottage in Clinton Corners

4.95 out of 5 average rating, 211 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.

Top guest favorite

Cottage in Rhinebeck

4.99 out of 5 average rating, 151 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.

Guest favorite

Cottage in New Milford

4.95 out of 5 average rating, 200 reviews

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.

Guest favorite

Cottage in Rhinebeck

4.92 out of 5 average rating, 152 reviews

Intimate Cottage on Private Estate

Bulls Head Cottage is a thoughtfully-designed retreat nestled within a 2.5 acre estate 5 minutes from Omega Institute and 10 minutes from the charming Village of Rhinebeck. The 720 square foot guest cottage is a relaxing place for up to 2 guests, offering cozy indoor and outdoor space including an office overlooking the property's pond. Enjoy quick access to hiking, shopping, fine dining and more. Under 2 hours from New York City by car or train. Pets not typically allowed.

Top guest favorite

Cottage in Pine Plains

4.99 out of 5 average rating, 137 reviews

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!

Superhost

A sunny view of the country cottage’s exterior showcases a large, grassy yard framed by a mature tree. The inviting porch features a couple of wooden chairs, while pastures and trees extend into the distance, creating a serene rural setting.

Cottage in North East

4.86 out of 5 average rating, 154 reviews

Sunset Cottage: Unplug - Relax - Recharge

Charming country cottage in Millerton, New York with a variety of nearby destinations. Unwind on a quiet country road with cows as your closest neighbors. Use as a base to explore the Tri-State area. Perfect for Parent Weekends for the nearby private schools. An idyllic setting in which to unplug and enjoy nature. Walk to the 42-mile Rail Trail, strap your bikes, skis, kayaks, or canoes to the car because you’ll be centrally located for adventure!

Top guest favorite

Cottage in Red Hook

4.98 out of 5 average rating, 249 reviews

CoZy Newly Renovated Cottage in Red Hook Village

'Solas Na Gréine' (Meaning 'light of the sun' in Irish) - Beautifully renovated private cottage located in the Village of Red Hook, New York. A perfect Hudson Valley getaway anytime of the year. Just 2 blocks (3 minute walk) to the town's center with wonderful cuisine, shops & small town charm. A short 5 minute drive to Bard College Campus, Hiking Trails, Orchards, Farms, & Wineries. Come relax, enjoy & explore upstate NY, just 90 miles from NYC.

Guest favorite

The exterior of the stone cottage is framed by lush autumn foliage. A spacious wooden deck features several lounge chairs, providing a relaxing outdoor space. The entrance is marked by a subtle stone pathway, enhancing the inviting appeal of the cottage.

Cottage in Pawling

4.98 out of 5 average rating, 121 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.

Top guest favorite

Cottage in Port Ewen

4.99 out of 5 average rating, 155 reviews

Swan Cottage with Expansive Hudson River Views

The Swan Cottage was built in 1923 and was fully renovated in 2020. The idyllic location, on a bluff overlooking the Hudson River, is the perfect perch to relax and get away from it all. The front porch is a nice spot to have a cup of coffee and watch the sailboats on the river, while the huge wraparound porch affords terrific views of the river as well as the forest that gives this home a feeling of being high in the tree tops.

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.

Top guest favorite

A wooden railing outlines a spacious deck, providing a view of a gently flowing creek bordered by lush greenery. Sunlight filters through the trees, highlighting the tranquil waters and surrounding vegetation.

Cottage in Staatsburg

4.91 out of 5 average rating, 193 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".