A large, historic building with a symmetrical facade, green shutters, and a central entrance with steps leading up to it.

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Top Cities in Dutchess County

A river with boats docked on the shore, surrounded by autumn-colored trees.
CottagesCottages

Poughkeepsie

Poughkeepsie

Our top choices for Dutchess County cottages

Property grounds

1. Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock
Woodstock
10.0 out of 10, Exceptional, (297 reviews)
"Wonderful property with an easy check in and checkout process. The property and surrounding areas are beautiful. We would stay here again. "
United States
Anonymous traveller
The price is CA $198
CA $435 total
includes taxes & fees
Sep 28 - Sep 29
Streamside Cottage Half Mile to Town of Woodstock
Exterior

2. Summer Lake Cottage, private beach, Berkshire Hills, small village

Summer Lake Cottage, private beach, Berkshire Hills, small village
Lakeville
9.6 out of 10, Exceptional, (90 reviews)
"The guys love this place. We have been coming for 3 years in a row and will be back next year."
United States
Chris M.
Summer Lake Cottage, private beach, Berkshire Hills, small village
Terrace/patio

3. Mountain View escape

Mountain View escape
New Paltz
10.0 out of 10, Exceptional, (90 reviews)
"This delightful cottage is remarkably well designed and stocked with everything a traveler could want. Huge yard, view of Mohonk mountain, comfortable king bed, excellent shower and pet friendly! We cooked all of our meals during our three night stay and lounged in the many outdoor spaces when we weren't hiking in Mohonk Preserve or driving the country roads. Host was super responsive and has put a lot of thought and love into the property. Loved it!"
United States
Susan
Mountain View escape
Living area

4. Tranquil 1 bedroom cottage with King size bed & Fireplace in charming Bethel, CT

Tranquil 1 bedroom cottage with King size bed & Fireplace in charming Bethel, CT
Bethel
10.0 out of 10, Exceptional, (16 reviews)
"Just a wonderful place to stay! We will be back…"
United States
Carole R.
Tranquil 1 bedroom cottage with King size bed & Fireplace in charming Bethel, CT
Property grounds

5. 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, (144 reviews)
"We had a great stay!!"
United States
Jasmine
The price is CA $273
CA $458 total
includes taxes & fees
Sep 16 - Sep 17
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Living area

6. 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, (63 reviews)
"Clean and welcoming cottage in a great location. We would definitely stay there again. "
United States
Tanya R.
Lily Cottage - a cozy accomodation moments from the beautiful Ashokan reservoir
Terrace/patio

7. Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill

Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
Catskill
9.8 out of 10, Exceptional, (19 reviews)
"The property was just as described, very private and cozy. We enjoyed the large balcony as well as the yard. There were also several nice hiking trails close by. Overall we were very happy with our stay."
United States
Ryan P.
The price is CA $160
CA $407 total
includes taxes & fees
Sep 14 - Sep 15
Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
Property grounds

8. Magnificent View on Whaley Lake

Magnificent View on Whaley Lake
Holmes
"Great Place to stay, and friendly host!"
United States
Noah L.
Magnificent View on Whaley Lake
Property grounds

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

Country Cottage with beautiful views and easy access to Catskills activities.
Saugerties
9.8 out of 10, Exceptional, (21 reviews)
"Very cozy, pictures represented it well"
United States
Kelly H.
Country Cottage with beautiful views and easy access to Catskills activities.
Exterior

10. Lakeview property in private community. Lake & beach access. Swim/Kayak all day!

Lakeview property in private community. Lake & beach access. Swim/Kayak all day!
Bethlehem
9.4 out of 10, Exceptional, (19 reviews)
"Adorable rustic lake cottage. The area has so many beautiful hiking trails, waterfalls, and historic house and garden museums. There are plenty of cozy restaurants nearby"
United States
Anonymous traveller
Lakeview property in private community. Lake & beach access. Swim/Kayak all day!
Exterior

11. 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, (94 reviews)
"Adorable cottage built in 1939. Close to town and well maintained."
United States
Julie Ann C.
ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi
Exterior

12. Two Bedroom Cottage Close To Town

Two Bedroom Cottage Close To Town
Sharon
9.2 out of 10, Wonderful, (36 reviews)
"Cagney’s home was so comfy! We loved the spacious family room. The beds were comfortable and the fully stocked kitchen made cooking much easier. Absolutely would love to stay at your cottage again!"
United States
Heidi F.
Two Bedroom Cottage Close To Town
Exterior

13. Relaxing Catskill Mountain Cottage.

Relaxing Catskill Mountain Cottage.
West Shokan
10.0 out of 10, Exceptional, (73 reviews)
"What a wonderful stay. "
United States
Emily C.
Relaxing Catskill Mountain Cottage.
Property grounds

14. Summer fun on the river. Swim, fish, kayak and bird watch at Croton River Gorge.

Summer fun on the river. Swim, fish, kayak and bird watch at Croton River Gorge.
Croton-on-Hudson
9.6 out of 10, Exceptional, (23 reviews)
"A lovely spot, very nice accommodations.Breakfast supples thoughtfully supplied as well as champagne to enjoy. "
United States
Eva C.
Summer fun on the river. Swim, fish, kayak and bird watch at Croton River Gorge.
Exterior

15. Charming Artist's Retreat

Charming Artist's Retreat
Saugerties
10.0 out of 10, Exceptional, (155 reviews)
"Such a beautiful spot! Convenient location that still felt like a peaceful retreat."
United States
Emily C.
Charming Artist's Retreat
Property grounds

16. Woodsy Country Cottage, HITS Horse Show, Fall Foliage, Skiing, Hunter Mt, Hiking

Woodsy Country Cottage, HITS Horse Show, Fall Foliage, Skiing, Hunter Mt, Hiking
Saugerties
10.0 out of 10, Exceptional, (97 reviews)
"Always a wonderful place to stay!"
United States
Sallyann S.
Woodsy Country Cottage, HITS Horse Show, Fall Foliage, Skiing, Hunter Mt, Hiking
Interior

17. Reset and Relax in Luxury Cottage

Reset and Relax in Luxury Cottage
Rhinebeck
10.0 out of 10, Exceptional, (54 reviews)
"We had a wonderful holiday weekend stay at the cottage! The cottage was even more lovely than the pictures show. There is a very nice deck and outdoor seating area too. Everything was extremely clean and well thought out to ensure you have everything you need for your stay. Our hosts were very friendly and quick to respond to any questions. We hope to visit again!"
United States
Kris M.
Reset and Relax in Luxury Cottage
Exterior

18. The Blue Elm - A Historic Berkshire Cottage

The Blue Elm - A Historic Berkshire Cottage
Sheffield
10.0 out of 10, Exceptional, (18 reviews)
"The space was even nicer than shown in the pictures and the owners were very friendly and provided helpful recommendations for places to eat and things to do in the area."
United States
M.S. H.
The Blue Elm - A Historic Berkshire Cottage
Living area

19. Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Goshen
9.2 out of 10, Wonderful, (14 reviews)
"Great place to stay when visiting Legoland. Convenient location and comfortable and clean."
United States
Jessica C.
The price is CA $205
CA $406 total
includes taxes & fees
Sep 9 - Sep 10
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Exterior

20. Herb Cottage-Historic Artist's Cottage in Woodstock: Wood Stove, Walk to Town!

Herb Cottage-Historic Artist's Cottage in Woodstock: Wood Stove, Walk to Town!
Woodstock
9.8 out of 10, Exceptional, (141 reviews)
"Great cozy place - awesome location."
United States
Eric F.
Herb Cottage-Historic Artist's Cottage in Woodstock: Wood Stove, Walk to Town!
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

Quality Inn Hyde Park Poughkeepsie North

Quality Inn Hyde Park Poughkeepsie North

8/10 Good
"Great staff, property is clean but is a bit worn down. Highlight was the staff, the location is convenient."
Satyaki 1-night trip
Posted 3 hours ago
Quality Inn Hyde Park Poughkeepsie North

Find out more about Dutchess County

Dutchess County Cottages information

Number of reviews
1,266
Accommodation
342 Cottages
Lowest Price
CA $406
Highest Price
CA $458

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