Cottage vacation rentals in Dutchess County

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Top-rated cottage rentals in Dutchess County

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Guest favorite

Cottage in Clinton Corners

4.95 out of 5 average rating, 196 reviews

brand new (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.

Guest favorite

Cottage in West Park

4.84 out of 5 average rating, 208 reviews

Rustic, Sunny, Little Red Cottage in the Woods

Just outside of New Paltz, the cottage is 400 square feet, plus loft area, in addition to a 120-square-foot (winterized) screened-in porch with bistro table and additional relaxation spots. The main room hosts a double-size, comfortable futon couch, a dining table for four or more, a fully equipped kitchen providing all the basic amenities. The loft (up a ladder) hosts a super-comfy queen-sized bed. There is a small stone patio with an outdoor dining table with umbrella and a barbeque grill.

Guest favorite

Cottage in Rhinebeck

4.99 out of 5 average rating, 138 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 Saugerties

4.97 out of 5 average rating, 101 reviews

Cottage on the creek with wonderful waterfall view

A sweet cottage with waterfall and creek view. It’s a well equipped cozy nest to rest & read. You can put up the hammock in the living room and just 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 short trips 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!

Superhost

Cottage in Rhinebeck

4.93 out of 5 average rating, 261 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

Cottage in Red Hook

4.98 out of 5 average rating, 635 reviews

bright serene + spacious barn

a bright serene space built by locals on the property we live on. we are in what we think is the most beautiful notch 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, at gallatin farmstead!

Superhost

Cottage in Kent

4.87 out of 5 average rating, 200 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

Guest favorite

Cottage in Pine Plains

4.98 out of 5 average rating, 130 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

Cottage in Rhinebeck

4.88 out of 5 average rating, 169 reviews

Secluded peaceful loft in barn by woods

La Barn Bleue sits on top of a hill by a forest, in a secluded and peaceful property. The main house, where we live is 150 feet down the hill. The apartment sleeps up to 4 people. The bedroom/lounge loft has one king bed and 2 twin beds. Ideal for families and kids above 5 years old. Because we used a rope railing, we cannot host kids under 5 years old for security reasons. We offer Wifi, AC/heat split unit, outdoor Picnic table, bbq, petanque court and pool!

Guest favorite

Cottage in North East

4.86 out of 5 average rating, 148 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!

Guest favorite

Cottage in Pawling

4.98 out of 5 average rating, 104 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.

Guest favorite

Cottage in Port Ewen

4.99 out of 5 average rating, 131 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.