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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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Top guest favorite

A cozy living room features two light-colored sofas adorned with soft throw pillows and a warm blanket. A wooden coffee table holds a potted plant and magazines. A large window offers a view of the outdoors, while bright artwork adds a personal touch to the space.

Cottage in Saugerties

4.97 out of 5 average rating, 143 reviews

Cottage on the creek with wonderful waterfall view

A sweet cottage with waterfall and creek view. There’s a creek side deck to relax and watch the creek & an outdoor shower. It’s a well equipped cozy nest to rest & read & relax all day. Set up your laptop in the dining nook and watch the birds as you work, or just unplug and nap on the couch. A great home base to come back to after to nature, hiking, skiing or just walking up to town to the bookstore for a game of chess and a cappuccino,. Whatever you choose to do, I hope you go home refreshed

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, 230 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

A charming two-story cottage is surrounded by trees, with a lush green hillside in the backdrop. The driveway leads to a garage with two entrance doors. An outdoor staircase ascends to the living area, illuminated by dappled sunlight filtering through the leaves.

Cottage in Pawling

4.97 out of 5 average rating, 105 reviews

Forest Acres Cottage: Appalachian/Empire St Trail!

This charming, stand alone cottage was completely renovated to welcome you to the picturesque Hudson Valley. Secluded porch overlooks a peaceful forest. Fast wi-fi, high end mattresses, cozy linens, fully stocked cook's kitchen and gas stove. Located on one of the area's most scenic roads yet close to major highways, Metro-North railroad and Hudson Valley delights. Three Empire State Rail Trail and two Appalachian access points merely 5-10 minute drive. Bring your bikes and walking shoes!

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, 304 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

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, 215 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.

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

4.93 out of 5 average rating, 173 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

The cozy cottage is surrounded by a lush green lawn, with a wooden deck and twinkling string lights creating a charming ambiance. A vibrant flower bed with sunflowers adds a splash of color, while the nearby creek offers serene water views.

Cottage in Saugerties

5 out of 5 average rating, 412 reviews

Carriage House on Falls, Walk to Village

Welcome to 1903 Carriage House on the Falls — just down the hill from the vibrant village of Saugerties. This cottage blends modern comfort with rustic charm. Its cozy size makes it the ultimate escape for couples seeking a tranquil getaway. Admire panoramic creek vistas from the back deck. Enjoy the outdoors with a gas grill and waterside gazebo, unwind with board games, or relax with a movie on the SmartTV. As night falls, drift off to the soothing sound of the waterfall.

A two-story home is surrounded by vibrant autumn foliage. The house features beige siding, black shutters, and a welcoming front porch. Two bright red garage doors complement the exterior, while a spacious driveway leads to the home, providing a serene and inviting entrance.

Cottage in Kent

4.81 out of 5 average rating, 254 reviews

NEW - Hot Tub - Mohawk Mtn - Appalachian Trl

Equipped with essentials such as air conditioning, cleaning products, cooking basics, and a dedicated workspace. Guests can prepare meals in the fully equipped kitchen, which includes dishes, silverware, and cooking utensils, dishwasher, and microwave. A washer and dryer, hair dryer, heating, and hot tub are also available for guests' use. 2 Min – Appalachian Trail 4 Min - Kent Town center 9 Min – Kent falls 10 Min - Bulls Bridge 19 Min - Mohawk Mountain Ski Area

A cozy living area features a light-colored couch with patterned cushions, illuminated by natural light. A television sits against a textured wall adorned with decorative plates. A dining table with modern chairs is visible, alongside an opening leading to a well-lit kitchen.

Cottage in Pine Plains

4.99 out of 5 average rating, 139 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!

Top guest favorite

An aerial view showcases a lakefront cottage with a warm-toned roof, surrounded by lush greenery. Two blue kayaks sit on the water, while a stone patio features a dining area. A fire pit adds to the outdoor space, blending with a wooden boat dock.

Cottage in Livingston

4.98 out of 5 average rating, 105 reviews

Waterlily Lakehouse - Modern+Waterfront+Retreat

The Waterlily House is a Lakefront cottage at the North Twin Lakes in Livingston, NY, located just 2 hours from NYC. The lakefront cottage has been designed and decorated in a Frandinavian Style (Parisian chic and Scandinavian minimalism ). This chic 4 bedroom, 3 bath home, which can sleep up to 8 people, has been designed with an eye for detail, style, and relaxation. Follow us on IG @waterlilylakehouse for any last-minute cancellations/openings

Top guest favorite

An interior corridor is visible, featuring rustic wooden beams and a warm wood floor. To one side, a glass-paneled room can be seen, likely housing a cozy nook. Light enters from multiple sources, creating an inviting and bright atmosphere.

Cottage in Red Hook

4.98 out of 5 average rating, 687 reviews

bright serene + spacious barn @barn and bike

a bright serene space built by locals on the property we live on. we are in what we think is the most beautiful region of the Hudson River Valley - surrounded by pastoral beauty and dramatic landscapes. quaint yet cultured towns in all directions. please read the entire description & rules before booking • beyond 2 guests, the rate adds 50$/night/per person • please add dogs (2 max. 50$/per dog) when booking • we look forward to having you here!

The interior space features a high vaulted ceiling with skylights, allowing ample natural light. A stone fireplace serves as a focal point, complemented by a comfortable seating area. A wooden dining table and a kitchen island with a butcher block top are also present.

Cottage in Pawling

4.99 out of 5 average rating, 143 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.

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Popular amenities for Dutchess County cottage rentals

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

A charming single-story house is set against a partly cloudy sky. The exterior features light-colored siding and a welcoming front porch with steps leading up. A manicured lawn with green shrubbery surrounds the home, and a two-car garage is visible to the left.

Cottage in Kingston

4.95 out of 5 average rating, 58 reviews

Charming Cottage in Kingston - License #002740

A two-story home is surrounded by vibrant autumn foliage. The house features beige siding, black shutters, and a welcoming front porch. Two bright red garage doors complement the exterior, while a spacious driveway leads to the home, providing a serene and inviting entrance.

Cottage in Kent

4.81 out of 5 average rating, 254 reviews

NEW - Hot Tub - Mohawk Mtn - Appalachian Trl

A large grassy yard is framed by mature trees, offering shade and a sense of serenity. A wooden swing set and a stone wall are visible, enhancing the rustic charm. The inviting home features large windows and a porch, blending seamlessly with the natural surroundings.

Cottage in Cold Spring

4.78 out of 5 average rating, 244 reviews

Cozy Countryside Cabin Spa/Fireplace/Enclosed Yard

Top guest favorite

A spacious backyard is featured, showcasing a charming cottage with a light-colored exterior. An inviting outdoor dining set with bright chairs is situated on the manicured grass. Surrounded by trees, the setting emphasizes tranquility, complemented by a birdhouse and additional green space.

Cottage in Hyde Park

5 out of 5 average rating, 67 reviews

Peaceful Hudson Valley Retreat with Hot Tub

Pet-friendly cottage rentals

The charming front porch features a bright pink door surrounded by hanging flower baskets. Stone tiles and wooden accents highlight the entrance, while columns provide structural support. Lush greenery is visible in the yard, offering a serene and welcoming environment.

Cottage in Ulster Park

4.94 out of 5 average rating, 97 reviews

West Park Cottage | Hiker's Paradise

A bright living room features large windows displaying a colorful sunset. A plush sectional sofa, dressed with several cushions, surrounds a round coffee table. A textured area rug adds warmth to the space, enhancing the inviting and comfortable atmosphere.

Cottage in New Fairfield

4.96 out of 5 average rating, 46 reviews

Sunset Cabin Modern Home Kayak FirePit Lake Access

A wooden deck is surrounded by lush greenery, featuring two lounge chairs positioned for relaxation. A charming cabin stands in the background, accentuated by a mix of trees and plants that create a secluded atmosphere.

Cottage in Carmel Hamlet

4.84 out of 5 average rating, 184 reviews

Lake Cabin Escape–Fenced Yard+Firepit.Dogs welcome

Top guest favorite

A contemporary cottage is nestled among lush greenery, featuring a dark exterior that complements the surrounding natural landscape. Colorful flower beds are present in the foreground, while trees create a serene backdrop, enhancing the feeling of seclusion in a nature preserve.

Cottage in Ulster Park

5 out of 5 average rating, 62 reviews

Nestled in Hudson River nature park near Kingston

Top guest favorite

A charming farmhouse is set amidst blooming trees and vibrant yellow flowers, approached by a winding gravel driveway. The single-level structure features a welcoming front porch and large windows, surrounded by lush greenery and a peaceful natural landscape.

Cottage in Saugerties

4.95 out of 5 average rating, 66 reviews

Catskills/Saugerties/Woodstock 50+ Acre Farmhouse!

A modern living area features a sleek black sofa adorned with colorful accent pillows, complemented by a striped bench in the center. A round tray sits on the bench, and light filters in through the nearby window, illuminating the textured area rug beneath.

Cottage in Kingston

4.96 out of 5 average rating, 48 reviews

Empire Bicycle Lodge

Top guest favorite

A cozy living space features a modern gas fireplace centrally placed against a white brick wall. Two stylish chairs with black woven seats are positioned beside the fireplace, while a natural wood table adds warmth. A patterned rug enhances the inviting atmosphere of the room.

Cottage in Red Hook

4.99 out of 5 average rating, 89 reviews

Creekside Cottage | The Fitz House Red Hook NY

A spacious living area features a vintage brick fireplace with a warm fire. Comfortable seating includes green and gray sofas, accented by a vibrant orange throw. Large windows allow natural light to fill the room, with wooden beams enhancing the airy design.

Cottage in Ancram

4.94 out of 5 average rating, 65 reviews

Cozy Country Home on 5 acres | Hudson 20 min

Private cottage rentals

A charming cottage is set against a backdrop of clear blue skies and scattered clouds. The exterior features white siding and a mix of large trees and fallen leaves in the foreground. A cozy extension with glass doors provides a glimpse of indoor space, enhancing the cottage's tranquil environment.

Cottage in Amenia

5 out of 5 average rating, 5 reviews

Quaint Country Cottage

A functional kitchen area features gray cabinetry and a white countertop, complemented by a window allowing natural light. A small dining table with chairs is set nearby, adorned with a vase of flowers. A coffee maker and kitchenware are also visible on the counter.

Cottage in Rhinebeck

4.81 out of 5 average rating, 98 reviews

Blue Cottage in Rhinebeck

A cottage with a rustic wooden exterior is nestled among trees in a lush green setting. A stone chimney rises from the roof, and a small set of steps leads to the entrance. Surrounding flora includes well-maintained shrubs and mulch, creating an inviting pathway.

Cottage in Cold Spring

4.96 out of 5 average rating, 23 reviews

Romantic Private Lake Art-Deco Cabin Hudson Valley

A bright living area showcases large windows dressed in soft orange drapes. A comfortable sectional sofa is positioned alongside two stylish chairs, centered around a glass-top table. An antique blue and white vase is displayed beside a traditional fireplace, enhancing the room's classic charm.

Cottage in Millbrook

4.97 out of 5 average rating, 65 reviews

Millbrook Cottage Originally a 1927 Sears Kit House

A rustic cottage exterior is framed by greenery, featuring weathered wooden walls and a sloped roof. A large tree stands beside the building, with a small porch visible and blue shutters adorning the windows. The property is set within a serene, natural landscape.

Cottage in Pleasant Valley

4.84 out of 5 average rating, 31 reviews

The Lucky Goat Farm

Top guest favorite

Cottage in Ulster Park

4.88 out of 5 average rating, 8 reviews

Leaf Peepers & Pumpkin Pickers- Bring Your DOGS!

The exterior of the Quarry Cottage features a blue siding and a welcoming front door. Lush green grass surrounds the cottage, with flower planters on either side of the entry. A stone patio is visible in the background, providing a tranquil outdoor space.

Cottage in Rhinebeck

4.93 out of 5 average rating, 14 reviews

Modern Quarry Cottage near Rhinebeck & Omega

An open-concept living space features a modern kitchen with stainless steel appliances and a dining area with a wooden table. A cozy seating area includes a gray sofa positioned near a fireplace. Natural light filters through sheer curtains, creating an inviting ambiance.

Cottage in Kingston

4.89 out of 5 average rating, 139 reviews

Modern, Lakeside Cottage

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