Cottages in Dutchess County

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Top Cities in Dutchess County

Our top choices for Dutchess County cottages

Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock
Woodstock
10.0 out of 10, Exceptional, (276 reviews)
"The view in the snow was absolutely gorgeous and the size of the accommodations was perfect!"
United States
Abigail Y.
The price is AED 592
AED 1,234 total
includes taxes & fees
18 Apr - 19 Apr
Streamside Cottage Half Mile to Town of Woodstock

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (134 reviews)
"Amazing place Thanks for the stay "
United States
Julien C.
The price is AED 691
AED 984 total
includes taxes & fees
19 Apr - 20 Apr
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Mountain View escape

Mountain View escape
New Paltz
10.0 out of 10, Exceptional, (79 reviews)
"Beautiful place, great and responsive host, highly recommend."
United States
Anell H.
Mountain View escape

Relaxing Catskill Mountain Cottage.

Relaxing Catskill Mountain Cottage.
West Shokan
10.0 out of 10, Exceptional, (63 reviews)
"Fantastic stay at this mountain cottage. We had everything we expected, and more!"
United States
Jordi C.
Relaxing Catskill Mountain Cottage.

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

Private Woodstock Retreat • In Town • Hot Tub • Dog Friendly
Woodstock
9.8 out of 10, Exceptional, (138 reviews)
"Fantastic location. Close to everything in townAnd quiet. I loved the second living room in the loft. "
United States
andrew m.
Private Woodstock Retreat • In Town • Hot Tub • Dog Friendly

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

Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
New Marlborough
9.6 out of 10, Exceptional, (22 reviews)
"This cottage was so cozy! So close to Great Barrington too. Loved being in the woods and hearing the trees. The place was clean and the owner answered questions quickly. We will definitely be back!"
United States
Aaron B.
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

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

TOP-RATED! Pristine style+romantic luxury+firepit+walk to town=Brook Cottage Too
Woodstock
10.0 out of 10, Exceptional, (124 reviews)
"Loved the property..beautiful and serene but so convenient to town!"
Australia
Carol G.
TOP-RATED! Pristine style+romantic luxury+firepit+walk to town=Brook Cottage Too

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

Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
Woodstock
10.0 out of 10, Exceptional, (82 reviews)
"We had a great stay at the Junebug Cottage. It was a great location, and our hosts were amazing."
United States
Anonymous traveler
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green

Charming loft cottage in tranquil Germantown with WiFi, AC

Charming loft cottage in tranquil Germantown with WiFi, AC
Germantown
10.0 out of 10, Exceptional, (10 reviews)
"Very clean, comfortable, good location, great communication with host. "
United States
Lisa B.
The price is AED 400
AED 794 total
includes taxes & fees
23 Apr - 24 Apr
Charming loft cottage in tranquil Germantown with WiFi, AC

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
woodstock
9.0 out of 10, Wonderful, (47 reviews)
"A gem just minutes from the heart of Woodstock!"
United States
Susannah H.
The price is AED 661
AED 1,140 total
includes taxes & fees
19 Apr - 20 Apr
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

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

Lily Cottage - a cozy accomodation moments from the beautiful Ashokan reservoir
Olivebridge
10.0 out of 10, Exceptional, (55 reviews)
"Very thoughtful, and communicative hosts. We had a wonderful stay. Would love to be back when in the area!"
United States
Avinava R.
Lily Cottage - a cozy accomodation moments from the beautiful Ashokan reservoir

Cozy, private and modern Cottage

Cozy, private and modern Cottage
Hudson
9.8 out of 10, Exceptional, (15 reviews)
"The house was cleaning and comfortable and the hot tub was very enjoyable for our stay."
United States
Daphne
Cozy, private and modern Cottage

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

ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi
Woodstock
9.8 out of 10, Exceptional, (90 reviews)
"A clean, warm and cozy cabin, excellent location. We thoroughly enjoyed our stay! "
United States
Henrikki H.
ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi

Wappinger Cottage - Scandinavian retreat on a creek

Wappinger Cottage - Scandinavian retreat on a creek
Poughkeepsie
10.0 out of 10, Exceptional, (30 reviews)
"Beautiful and clean cottage on an amazing and tranquil property. We loved every aspect of our stay!"
United States
Erik
Wappinger Cottage - Scandinavian retreat on a creek

Charming Artist's Retreat

Charming Artist's Retreat
Saugerties
10.0 out of 10, Exceptional, (148 reviews)
"Absolutely beautiful, cozy home with so much character. We loved our stay!"
United States
Bianca U.
Charming Artist's Retreat

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

Country Cottage with beautiful views and easy access to Catskills activities.
Saugerties
10.0 out of 10, Exceptional, (17 reviews)
"We stayed 2 nights with our dog. The cottage had everything we needed for our stay. "
United States
Debra S.
Country Cottage with beautiful views and easy access to Catskills activities.

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

Tannery Brook Cottage: Terraced Garden with Patio, Cascade and Fire Pit.
Woodstock
10.0 out of 10, Exceptional, (15 reviews)
"We had an amazing stay. Cottage is beautiful and has everything you need. Great communication with the host. "
United States
Erin O.
Tannery Brook Cottage: Terraced Garden with Patio, Cascade and Fire Pit.

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

Charming Cottage in Private Lake Community (Pet-Friendly!)
Athens
9.8 out of 10, Exceptional, (40 reviews)
"We enjoyed our stay over Thanksgiving 2025. Cozy and quiet, about 25 rural minutes outside of Catskill/Hudson made for easy day trips. "
United States
Kimberly S.
Charming Cottage in Private Lake Community (Pet-Friendly!)

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

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks
Kerhonkson
9.6 out of 10, Exceptional, (14 reviews)
"Charming and relaxing cottage. Perfect location for hiking or enjoying Lake Minnewaska or Mohonk Preserve. "
United States
Patrick S.
The price is AED 290
AED 648 total
includes taxes & fees
30 Apr - 1 May
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

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

Woodstock Cottage with hot tub. Close to town yet very private.
Woodstock
9.4 out of 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!"
United States
Stephen
Woodstock Cottage with hot tub. Close to town yet very private.
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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Top Dutchess County Hotel Reviews