Top Cottages in Dutchess County in 2026

A lake surrounded by hills with autumn foliage, a small island with a historic building, and a cloudy sky.

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Our top choices for Dutchess County cottages

A covered outdoor seating area with a sofa, chairs, and a table.

1. Historic Barn Retreat w/ Pool & Pond Views Longview Pond Lodge by Avantstay

Clinton Corners

Dieter

An outdoor dining area with a table set for two, a hot tub, and a view of a modern building with large windows.

2. Luxe Mountain Getaway on Private Rd Near Rhinebeck

Hyde Park

A single-story house with a brick chimney, a front door, and a small patio with outdoor furniture.

3. Modern NY Home w/ Views By Hudson Valley Hiking!

Hopewell Junction

A covered patio with a red umbrella, a round table, and metal chairs.

4. Hudson Valley Horse Farm Retreat in Salt Point

Salt Point

A covered wooden deck with a table and chairs, white railings, and a view of greenery.

5. Fire Pit + On-site Pond: Hudson Valley Home!

Wappingers Falls

Cheryl

A deck with a grill, outdoor furniture, and a view of trees.

6. Heated Pool, 6 Acres: Beacon Area Vacation Rental

Lagrangeville

A pathway leading to a wooden house with a stone wall and a wooden deck.

7. Pet-friendly Hopewell Junction Home w/ Pool

Hopewell Junction

Anonymous traveler

A modern two-story house with a large front yard, wooden deck, and outdoor seating area.

8. Hudson Valley Summer Escape w/ Pool & Fire Pit

Pine Plains

A rural landscape with a large barn, a tennis court, and a pond.

9. The Bear Barn by Avantstay 150-acre Historic 1860 Barn Fire Pit + Mountain Views

Dover Plains

A wooden deck with wicker furniture and a white railing.

10. Hudson Valley Vacation Rental: Near Hiking

Beacon

A two-story house with a front porch, surrounded by dense trees.

11. Preston House by Avantstay Book-lined Library + Sunroom + Dining for 8 Near Hiking Trails + Metro-north

Dover Plains

A two-story house with a gabled roof and a front porch.

12. Walk to Downtown: Pet-friendly Millerton Home!

Millerton

13. Stunning Pawling Retreat w/ Ponds & Waterfall

Pawling

14. Hudson Valley Vacation Rental Near Rhinebeck!

Rhinebeck

A large, two-story house with a stone facade, a front porch, and a well-maintained lawn.

15. The Lake Ellis Lodge by Avantstay Sleeps 24 Private Lake + Beach + Dock Pool + Chef's Kitchen

Wingdale

A two-story house with a stone chimney, a porch, and a white fence in the foreground.

16. East Mt Cabin by Avantstay 1700s Farmhouse Stone Fireplace + Big Lawn + Appalachian Trail

Wingdale

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Top Dutchess County Hotel Reviews

Hampton Inn & Suites Poughkeepsie

8/10 Good

"Ok"

Quality Inn Hyde Park Poughkeepsie North

8/10 Good

"This was a very nice stay, almost perfect. Room was clean and smelled good. We had a king sized bed and it was very comfortable. Plenty of towels, soaps, shampoo etc. everything was in good condition, ie TV, fridge, microwave, iron etc. the location is great! In walking distance to a couple of restaurants and very close to the Vanderbilt and Rockefeller mansions. My negative comments are very minor and picky but if these few adjustments are made it would be absolutely perfect. Breakfast was basic and good, if only they could crisp up the sausages, because I assumed they were microwaved they kind of had a fleshy texture. They had eggs, sausage, cereal, yogurts, coffee, juices, a great waffle maker and packaged danish. Overall it was decent. My only other suggestion is the gym. We always use the gym wherever we stay. They need to upgrade the treadmill and the elliptical, they are on the cheaper end and it shows. They also need to keep it cooler in there, hard to work out long because it gets too hot. Other than that I would highly recommend staying there and will definitely revisit if I am in the area again."

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Dutchess County Cottages information

Number of reviews	6
Accommodation	214 Cottages
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