Top Cottages in Dutchess County in 2026

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Top Cities in Dutchess County

Poughkeepsie

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Our top choices for Dutchess County cottages

Cottage in Woodstock

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (271 reviews)

10/10

Exceptional

(271 reviews)

"Jane was very nice and accommodating, the cottage was very clean and comfortable, a very relaxing and calming place "

Scott

Streamside Cottage Half Mile to Town of Woodstock

1 bedroom, desk, iron/ironing board, free WiFi

Cottage in Fort Montgomery

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (132 reviews)

9.8/10

Exceptional

(132 reviews)

"Amazing place Thanks for the stay "

Julien C.

The price is HK$1,472

HK$1,472

HK$2,382 total

includes taxes & fees

16 Mar - 17 Mar

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

1 bedroom, desk, iron/ironing board, WiFi

Cottage in New Paltz

Mountain View escape

10.0 out of 10, Exceptional, (78 reviews)

10/10

Exceptional

(78 reviews)

"The home was amazing. So cozy and well kept, we had a great time here! We can’t wait to be back!"

Hailey C.

Mountain View escape

Cottage in West Shokan

Relaxing Catskill Mountain Cottage.

10.0 out of 10, Exceptional, (59 reviews)

10/10

Exceptional

(59 reviews)

"Fantastic stay at this mountain cottage. We had everything we expected, and more!"

Jordi C.

Relaxing Catskill Mountain Cottage.

Cottage in New Marlborough

Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

9.6 out of 10, Exceptional, (20 reviews)

9.6/10

Exceptional

(20 reviews)

"Great fall destination with beautiful scenery and serene lake a short walk away"

Melvin E.

Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

Cottage in Woodstock

Private Woodstock Retreat • In Town • Hot Tub • Dog Friendly

9.8 out of 10, Exceptional, (134 reviews)

9.8/10

Exceptional

(134 reviews)

"The property was adorable and host was very attentive. The perfect property for a girls trip!"

Angelina B.

Private Woodstock Retreat • In Town • Hot Tub • Dog Friendly

Cottage in Woodstock

TOP-RATED! Pristine style+romantic luxury+firepit+walk to town=Brook Cottage Too

10.0 out of 10, Exceptional, (124 reviews)

10/10

Exceptional

(124 reviews)

"Loved the property..beautiful and serene but so convenient to town!"

Carol G.

TOP-RATED! Pristine style+romantic luxury+firepit+walk to town=Brook Cottage Too

Fridge, microwave, coffee/tea maker, electric kettle

Cottage in Woodstock

Junebug Cottage: peace, love and privacy a short walk to Woodstock village green

10.0 out of 10, Exceptional, (81 reviews)

10/10

Exceptional

(81 reviews)

"We had a great stay at the Junebug Cottage. It was a great location, and our hosts were amazing."

Anonymous traveller

Junebug Cottage: peace, love and privacy a short walk to Woodstock village green

Cottage in Germantown

Charming loft cottage in tranquil Germantown with WiFi, AC

10.0 out of 10, Exceptional, (10 reviews)

10/10

Exceptional

(10 reviews)

"Very clean, comfortable, good location, great communication with host. "

Lisa B.

The price is HK$853

HK$853

HK$1,657 total

includes taxes & fees

16 Mar - 17 Mar

Charming loft cottage in tranquil Germantown with WiFi, AC

Cottage in Olivebridge

Lily Cottage - a cozy accomodation moments from the beautiful Ashokan reservoir

10.0 out of 10, Exceptional, (54 reviews)

10/10

Exceptional

(54 reviews)

"Lily Cottage was a warm cozy and clean base camp for us. I will definitely stay here again when I return to the area!"

William M.

Lily Cottage - a cozy accomodation moments from the beautiful Ashokan reservoir

Cottage in woodstock

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

9.0 out of 10, Wonderful, (47 reviews)

9.0/10

Wonderful

(47 reviews)

"A gem just minutes from the heart of Woodstock!"

Susannah H.

The price is HK$1,409

HK$1,409

HK$2,429 total

includes taxes & fees

22 Mar - 23 Mar

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

3 bedrooms, desk, iron/ironing board, free WiFi

Cottage in Poughkeepsie

Wappinger Cottage - Scandinavian retreat on a creek

10.0 out of 10, Exceptional, (29 reviews)

10/10

Exceptional

(29 reviews)

"Beautiful and clean cottage on an amazing and tranquil property. We loved every aspect of our stay!"

Erik

Wappinger Cottage - Scandinavian retreat on a creek

Cottage in Woodstock

ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi

9.8 out of 10, Exceptional, (88 reviews)

9.8/10

Exceptional

(88 reviews)

"A clean, warm and cozy cabin, excellent location. We thoroughly enjoyed our stay! "

Henrikki H.

ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi

Cottage in Saugerties

Country Cottage with beautiful views and easy access to Catskills activities.

10.0 out of 10, Exceptional, (16 reviews)

10/10

Exceptional

(16 reviews)

"We stayed 2 nights with our dog. The cottage had everything we needed for our stay. "

Debra S.

Country Cottage with beautiful views and easy access to Catskills activities.

Cottage in Hudson

Cozy, private and modern Cottage

10.0 out of 10, Exceptional, (12 reviews)

10/10

Exceptional

(12 reviews)

"The house was cleaning and comfortable and the hot tub was very enjoyable for our stay."

Daphne

Cozy, private and modern Cottage

Cottage in Woodstock

Woodstock Cottage with hot tub. Close to town yet very private.

9.4 out of 10, Exceptional, (90 reviews)

9.4/10

Exceptional

(90 reviews)

"We had a lovely time and the host was super responsive and caring. The property is lovely and cozy. The fireplace was super easy to use, the beds were comfortable, the amenities were plentiful. The home took a little while to warm up but we are almost at the start of winter and there is snow on the ground. Otherwise, great stay!"

Stephen

Woodstock Cottage with hot tub. Close to town yet very private.

3 bedrooms, iron/ironing board, free WiFi, bed sheets

Cottage in Athens

Charming Cottage in Private Lake Community (Pet-Friendly!)

9.8 out of 10, Exceptional, (40 reviews)

9.8/10

Exceptional

(40 reviews)

"Spent most of our time in Hudson for a family wedding, but great to come back to comfy accommodations. Very pet friendly too! Our dog enjoyed her walks in a new neighborhood.Great house for family getaways "

Lori C.

Charming Cottage in Private Lake Community (Pet-Friendly!)

Cottage in Woodstock

Tannery Brook Cottage: Terraced Garden with Patio, Cascade and Fire Pit.

10.0 out of 10, Exceptional, (15 reviews)

10/10

Exceptional

(15 reviews)

"Great location, excellent host and lovely home."

daniela b.

Tannery Brook Cottage: Terraced Garden with Patio, Cascade and Fire Pit.

Cottage in Saugerties

Charming Artist's Retreat

10.0 out of 10, Exceptional, (148 reviews)

10/10

Exceptional

(148 reviews)

"Absolutely beautiful, cozy home with so much character. We loved our stay!"

Bianca U.

Charming Artist's Retreat

Cottage in Kerhonkson

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

9.4 out of 10, Exceptional, (13 reviews)

9.4/10

Exceptional

(13 reviews)

"Charming and relaxing cottage. Perfect location for hiking or enjoying Lake Minnewaska or Mohonk Preserve. "

Patrick S.

The price is HK$590

HK$590

HK$1,430 total

includes taxes & fees

19 Mar - 20 Mar

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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