Cottage vacation rentals in Dutchess County

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Top-rated cottage rentals in Dutchess County

Guests agree: these cottages are highly rated for location, cleanliness, and more.

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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

The exterior of a cottage is shown, featuring a dark blue façade with a shingled roof and a central star accent. A welcoming porch is lined with four red chairs and decorative flower pots. Lush green grass and trees provide a serene setting.

Cottage in Clinton Corners

4.95 out of 5 average rating, 210 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.

Superhost

A wooden deck extends from the cabin, featuring a round table with two transparent chairs. The view includes a forest of bare trees under a setting sun, casting warm light across the space.

Cottage in Rhinebeck

4.93 out of 5 average rating, 281 reviews

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

Guest favorite

A rustic cottage is nestled among tall trees, overlooking a flowing brook. A wooden bench sits on a grassy area, with large boulders nearby. The house features a deck and is surrounded by greenery, with a gravel driveway leading up to the front.

Cottage in New Milford

4.95 out of 5 average rating, 196 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

The exterior of a charming cottage is seen, featuring a front porch with two black chairs and potted plants. Stone steps lead up to the entrance, flanked by shrubs and trees, creating a serene setting within the landscaped grounds.

Cottage in Rhinebeck

4.92 out of 5 average rating, 151 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

An outdoor dining area features a wooden table surrounded by two foldable chairs. A potted plant rests at the center of the table. In the background, a charcoal grill is positioned beside lush greenery and blooming flowers.

Cottage in Pine Plains

4.99 out of 5 average rating, 136 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!

Guest favorite

A gently flowing river meanders through lush greenery, with vibrant grasses and wildflowers lining the banks. Sunlight reflects off the water's surface, creating a shimmering effect. Dense trees provide a scenic backdrop to this serene natural setting.

Cottage in North East

4.87 out of 5 average rating, 151 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

An outdoor seating area is captured in soft evening light, featuring a rustic wooden backdrop and comfortable seating adorned with decorative pillows. Ambient lighting provided by pendant bulbs enhances the inviting feel of the space, which is framed by lush greenery.

Cottage in Red Hook

4.98 out of 5 average rating, 248 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

A bedroom features a spacious bed adorned with soft linens, positioned beneath large, angled windows that frame views of the surrounding greenery. A stone wall adds texture, while the ceiling fan promotes air circulation. Soft lighting from bedside lamps enhances the ambiance.

Cottage in Pawling

4.98 out of 5 average rating, 119 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

Aerial view of Swan Cottage displays a charming two-story structure surrounded by greenery. A spacious front porch, equipped with seating, is visible. Lounge chairs are arranged on the well-kept lawn, enhancing the outdoor space. The cottage features a welcoming layout amidst flourishing trees.

Cottage in Port Ewen

4.99 out of 5 average rating, 153 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

A small outdoor seating area features two metal chairs and a round table, surrounded by lush greenery. The view looks out onto a calm lake, partially obscured by foliage, creating a serene and private atmosphere.

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".

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What guests are saying

West Park/ Esopus Cottage - 2 King /1 Queen bed

4.95 out of 5 average rating, 22 reviews5 months ago

We loved Onora’s place. It was clean, comfortable, and cute, a well-updated historical home. The beds were comfy, kitchen well-appointed, and the yard and sunroom were very pretty. It was also very close to hiking, to the river, and a short drive from wineries, breweries, good food, and the very approachable and fun city of Kingston. Onora was communicative in advance and shared recommendations for food and activities. We highly recommend this airbnb!

Cottage in Esopus

What guests are saying

Hudson River view 1 block away, firepit in yard

4.98 out of 5 average rating, 96 reviews2 months ago

We had an amazing stay at Dawn’s house. She was very proactive, giving clear instructions for arrival and a manual with house rules and a ton of local recommendations for shops and things to do. The house was super cozy with plenty of blankets for movie marathons and games for game night (we especially loved playing backgammon). Dawn even left us Valentine’s Day treats for our arrival - such a wonderful experience!

Cottage in Port Ewen

What guests are saying

The Gallatin Farmhouse

4.97 out of 5 average rating, 59 reviews3 months ago

A lovely home for a super cozy winter weekend away in the country! For folks who like to cook, the full kitchen has everything you need, and for those with little ones, lots of great kid-friendly amenities throughout the house as well. A short, scenic drive from downtown Pine Plains, and an easy shot up to Hudson or over to Rhinebeck. Super responsive and congenial host! Would definitely stay again!

Cottage in Pine Plains

What guests are saying

Patchin Mills Quaint Country Cottage

5 out of 5 average rating, 140 reviews5 months ago

Cutest little cottage! Really loved the back porch / deck area. Loved this spot — affordable and perfect for a fall weekend getaway. Jeanine and Keith had lots of cute touches like homemade pumpkin bread and eggs in the fridge. They are also easy to communicate with. The town is very cute, too.

Cottage in Pine Plains

What guests are saying

Catskills/Saugerties/Woodstock 50+ Acre Farmhouse!

4.95 out of 5 average rating, 64 reviews2 months ago

The house was a great getaway, with a perfect location. It is only 5-10 minutes from the major highway, and gas station/grocery store. It is also situated right in between Saugerties and Woodstock, so it is perfect for exploring both towns. The house itself is comfy and has everything you need. There is an active farm next door, with some cows and animals you can see out the window! Although the farm is right there, the grounds are very peaceful and quiet. The WIFI worked well, and they had a fire stick / HDTV for entertainment. Laundry machines were also awesome to have during the snowy weather. If you are planning to come during the snow, I would suggest a AWD car, as the driveway is not paved and a bit bumpy getting up there. All in all, the host Ron was great and the house has everything you can ask for in a nice, peaceful vacation!

Cottage in Saugerties

What guests are saying

Carriage House on Falls, Walk to Village

5 out of 5 average rating, 379 reviews1 week ago

My Fiancée and I came here to celebrate our engagement and had the best time! We were greeted by a celebratory bottle of wine from the host which was a very nice touch! The carriage house felt very “home-y” and really allowed us to unplug from every day life and just enjoy time together! We can’t recommend Laura & Leo/The Carriage House enough! Hope to visit again soon!

Cottage in Saugerties

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