Cottage vacation rentals in Dutchess County

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Top-rated cottage rentals in Dutchess County

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Guest favourite

Cottage in Clinton Corners

4.94 out of 5 average rating, 162 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.

Jan. 6 – 13

$309 CAD per night

Guest favourite

Cottage in Pine Plains

5.0 out of 5 average rating, 132 reviews

Patchin Mills Quaint Country Cottage

Welcome to your cozy cottage in the bucolic Hudson Valley. Only 90 mi. north of NYC. We welcome small dogs, under 25 lbs. with prior host approval. Sorry, NO CATS. Enjoy biking, hiking, skiing, local culture or just relaxing. 1 mile outside a charming village in farm and horse country, your cottage has a full kitchen/LR, 2 BRS (1 queen, 1 full), bathrm, washer/dryer, deck, patio & yard. Close to colleges, dining & activities. We hope that you will love this corner of the world as much as we do.

Apr. 7 – 14

$272 CAD per night

Guest favourite

Cottage in Clinton Corners

4.89 out of 5 average rating, 155 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!

Sep. 27 – Oct. 4

$910 CAD per night

Guest favourite

Cottage in West Park

4.84 out of 5 average rating, 195 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.

Oct. 21 – 28

$184 CAD per night

Guest favourite

Cottage in Rhinebeck

4.94 out of 5 average rating, 120 reviews

Refined, Intimate Cottage on Private Estate

Built in 1930, 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.

Oct. 9 – 16

$401 CAD per night

Guest favourite

Cottage in Rhinebeck

4.95 out of 5 average rating, 232 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

Sep. 24 – Oct. 1

$293 CAD per night

Guest favourite

Cottage in Rhinebeck

4.99 out of 5 average rating, 120 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 "downtown" Rhinebeck, but also close to Red Hook, 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.

Jul. 15 – 22

$349 CAD per night

Superhost

Cottage in North East

4.86 out of 5 average rating, 130 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 bunnies , dairy and beef cows as your closest neighbors. Use as a base to explore the Tri-State area. Perfect for Parent Weekends for the nearby private schools. Get away from the stress: no Six O’clock news, no Wi-Fi, no beeping microwave. Strap the bikes, skis, kayaks, or canoes to the car because you’ll be centrally located for adventures.

Mar. 12 – 19

$215 CAD per night

Guest favourite

Cottage in Red Hook

4.98 out of 5 average rating, 598 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!

Nov. 14 – 21

$489 CAD per night

Guest favourite

Cottage in Pine Plains

4.98 out of 5 average rating, 119 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!

Sep. 19 – 26

$198 CAD per night

Guest favourite

Cottage in Rhinebeck

4.87 out of 5 average rating, 147 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!

Apr. 21 – 28

$245 CAD per night

Guest favourite

Cottage in Saugerties

5.0 out of 5 average rating, 314 reviews

Carriage House on Falls, Walk to Village

Welcome to 1903 Carriage House on the Falls. Recently remodeled, this retreat blends modern conveniences with old-world charm and original woodwork. Admire panoramic vistas up and down the Esopus Creek. It sits on a dead-end residential street, yet is only steps away from dining/shopping in the vibrant village of Saugerties. Gas grill, board games & SmartTV to enhance your stay. At night, crack a window and nod off to sound of the falls.

Sep. 1 – 8

$443 CAD per night