Top Cottages in Dutchess County in 2026

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

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Top Cities in Dutchess County

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

A suspension bridge over a river, surrounded by lush green hills.

Our top choices for Dutchess County cottages

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

Croton-on-Hudson

Eva C.

2. Streamside Cottage Half Mile to Town of Woodstock

Woodstock

Anonymous traveler

AED 1,169 total

includes taxes & fees

7 Sep - 8 Sep

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

Woodstock

Christopher

4. Charming Artist's Retreat

Saugerties

Richard L.

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

Saugerties

Sallyann S.

6. Wappinger Cottage - Scandinavian retreat on a creek

Poughkeepsie

Erik

7. Mountain View escape

New Paltz

Vicki C.

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

Saugerties

Kelly H.

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Top Dutchess County Hotel Reviews

Comfort Suites Fishkill near Interstate 84

10/10 Excellent

"Clean Room ; Large Bedroom Space ; Pleasant Staff , Wifi was okay due to location"

Mirbeau Inn & Spa Beacon

10/10 Excellent

"The staff was exceptionally friendly and accomodating. The grounds are really beautiful and sitting outside looking at the pool is very calming and peaceful. The dining rooms are very elegant but one of them in particualr is rather dark. Also, most of the chairs were very low, and for an elder person, hard to get out of, and for a short person, way too low for the table. Again, the staff was accomodating and found us a table with normal size chairs, but they shouldn't have to. The one thing I wish would be changed, and it's an easy change, is to provide one NON scented soap and body lotion. Everything is Eulcalyptus, which is a strong scent, and does not agree with all skin types. Especially with the added pepper, it can sting."

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

10/10 Excellent

"Hotel is beautiful. Staff were very friendly and helpful. Room was comfortable. Location was fantastic.....right in the midst of many restaurants and historical sites. Will definitely stay with them again if I'm in the area. Only negative was that they charge a daily parking fee. Should be included in cost of stay."

Cottages in Dutchess County

Change your mind

Treat yourself

Be picky

Check prices for these dates

Top Cities in Dutchess County

Poughkeepsie

Wappingers Falls

Our top choices for Dutchess County cottages

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

2. Streamside Cottage Half Mile to Town of Woodstock

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

4. Charming Artist's Retreat

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

6. Wappinger Cottage - Scandinavian retreat on a creek

7. Mountain View escape

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

9. Reset and Relax in Luxury Cottage

10. Charming Cottage in the Heart of the Shawangunks

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

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

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

14. Lakefront Brewster Vacation Rental w/ Private Dock

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

16. Cozy 2-bedroom cottage in peaceful Danbury with AC

17. Mtn-view Retreat in Huson Valley: Great for Groups

18. Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

19. Relaxing Catskill Mountain Cottage.

20. Magnificent View on Whaley Lake

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Top Dutchess County Hotel Reviews

Comfort Suites Fishkill near Interstate 84

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