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Holiday Homes in Dover Plains

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Dover Plains holiday homes

A spacious living room with a large wooden dining table, a comfortable sofa, and a bookshelf filled with books and decorative items.

1. Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway

Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
Millbrook
10.0 out of 10, Exceptional, (6 reviews)
"This is a charming, historic, well-maintained home on a beautifully landscaped lot. The updates in the home balance a respect for tradition while also providing modernization. The village of Millbrook is a quintessential twee New England village. The house felt very comfortable and homey and the caretaker was attentive and accommodating. We enjoyed our stay!"
United States
Beth E.
The price is €745
includes taxes & fees
4 Oct - 5 Oct
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

2. Cozy private room in a shared home with a Full-size bed and private bathroom.

Cozy private room in a shared home with a Full-size bed and private bathroom.
New Milford
10.0 out of 10, Exceptional, (1 review)
"Clean and close to activitys"
United States
randall
The price is €144
includes taxes & fees
13 Oct - 14 Oct
Cozy private room in a shared home with a Full-size bed and private bathroom.
A room with a bed, a couch, a desk with a computer, and various wall decorations.

3. Spacious 4-bedroom estate in adorable Carmel Hamlet with AC

Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
Carmel Hamlet
The price is €248
includes taxes & fees
29 Sept - 30 Sept
Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
A picnic setup with a checkered blanket, a basket, and two wine glasses on a grassy area with a lake and trees in the background.

4. Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
New Fairfield
8.6 out of 10, Excellent, (36 reviews)
"Very serene location, the host was very responsive and helpful."
United States
Stephen L.
The price is €308
includes taxes & fees
18 Oct - 19 Oct
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
A kitchen with wooden cabinets, a black countertop, a sink, and a window with a view of trees.

5. "Country outside the city " 3 bedrooms 2 full bathrooms

"Country outside the city " 3 bedrooms 2 full bathrooms
Holmes
9.6 out of 10, Exceptional, (4 reviews)
"Great house! We had a fantastic weekend!! Thank you so much "
United States
pamela w.
The price is €496
includes taxes & fees
30 Sept - 1 Oct
"Country outside the city " 3 bedrooms 2 full bathrooms
A living room with a television, a cabinet, a glass coffee table, and a framed picture on the wall.

6. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Stanfordville
The price is €605
includes taxes & fees
1 Oct - 2 Oct
Chic Lakeside Oasis|Near Rhinebeck & Millbrook
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

7. Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.4 out of 10, Exceptional, (13 reviews)
"Lovely space and situation, unique. Close to the AT, as well."
United States
Peter W.
The price is €253
includes taxes & fees
28 Sept - 29 Sept
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
A modern living room with a grey sofa, a wooden coffee table, and a staircase leading to an upper floor.

8. Chic Barn Style * Fireplace * Near Stissing House

Chic Barn Style * Fireplace * Near Stissing House
Pine Plains
10.0 out of 10, Exceptional, (3 reviews)
"We loved the property and everything was so welcoming! Having a pool there would be the best addition for this place!"
United States
Estefany G.
The price is €636
includes taxes & fees
28 Oct - 29 Oct
Chic Barn Style * Fireplace * Near Stissing House
A spacious living room with a fireplace, a dining area with a view of a lake, and a cozy seating arrangement.

9. Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Carmel Hamlet
9.8 out of 10, Exceptional, (20 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is €358
includes taxes & fees
5 Oct - 6 Oct
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
A modern kitchen with a granite countertop, a built-in stove, and a dining area with a glass table and chairs.

10. Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Poughkeepsie
9.6 out of 10, Exceptional, (5 reviews)
"Beautiful property with ample space for parking. Host was super nice and met all of our needs!"
United States
Nicole Y.
The price is €368
includes taxes & fees
28 Sept - 29 Sept
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
A room with a built-in bench along a wall with large windows, a door, and a tiled floor.

11. The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining

The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
New Milford
The price is €686
includes taxes & fees
28 Sept - 29 Sept
The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
An outdoor patio area with a covered seating area, a pool, and potted plants.

12. Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Fishkill
9.2 out of 10, Wonderful, (78 reviews)
"It’s was nice, clean and the outdoor out area was really nice."
United States
Roger S.
The price is €305
includes taxes & fees
30 Sept - 1 Oct
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
A modern kitchen with white cabinets, a built-in toaster, a blender, and a window with a view of trees.

13. Amazing 3-bedroom house with AC in adorable Highland

Amazing 3-bedroom house with AC in adorable Highland
Highland
The price is €467
includes taxes & fees
29 Sept - 30 Sept
Amazing 3-bedroom house with AC in adorable Highland
A large wooden dining table surrounded by chairs, with a stone fireplace and large windows in the background.

14. The George is an elegant restored home in the Hudson Valley

The George is an elegant restored home in the Hudson Valley
Stanfordville
9.6 out of 10, Exceptional, (10 reviews)
"Clean, comfortable, private, and plenty of room. Hosts went above and beyond to make our stay easy and memorable."
United States
Polly J.
The price is €979
includes taxes & fees
28 Sept - 29 Sept
The George is an elegant restored home in the Hudson Valley
A hot tub in a backyard with a house, trees, and a clear sky.

15. Las Flores Villa

Las Flores Villa
5.0 star property
New Preston
10.0 out of 10, Exceptional, (1 review)
The price is €3,077
includes taxes & fees
1 Oct - 2 Oct
Las Flores Villa
A stone house with a steeply pitched roof, surrounded by a well-maintained lawn and trees.

16. Chestnut on Willow Lake

Chestnut on Willow Lake
Fishkill
9.8 out of 10, Exceptional, (6 reviews)
"We really enjoyed the privacy of the grounds, lake, dock , swimming, boats and paddle boards. The kitchen was well equipped and the beds were comfy. We had a great stay, thanks."
United States
Doria W.
The price is €615
includes taxes & fees
28 Sept - 29 Sept
Chestnut on Willow Lake

17. Hudson Escape W/ Hot Tub + Bridge View

Hudson Escape W/ Hot Tub + Bridge View
Highland
The price is €843
includes taxes & fees
1 Oct - 2 Oct
Hudson Escape W/ Hot Tub + Bridge View
A modern kitchen with white cabinets, a large island, and a skylight.

18. A Country Lodge Straight Out of the Pages of a Great Novel

A Country Lodge Straight Out of the Pages of a Great Novel
Pine Plains
10.0 out of 10, Exceptional, (15 reviews)
"We loved the house and it really added to our upstate experience!!"
United States
stephen r.
The price is €1,271
includes taxes & fees
28 Oct - 29 Oct
A Country Lodge Straight Out of the Pages of a Great Novel
A stone house with a steeply pitched roof, surrounded by a well-maintained lawn and trees.

19. Hickory on Willow Lake

Hickory on Willow Lake
Fishkill
9.8 out of 10, Exceptional, (6 reviews)
"Clean, quiet and great location. Beautiful property."
United States
Sheila B.
The price is €676
includes taxes & fees
28 Sept - 29 Sept
Hickory on Willow Lake
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 Dover Plains Hotel Reviews

Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

10/10 Excellent
"Good"
Rebecca 1-night trip
Posted 9 hours ago
Hyatt Place Poughkeepsie / Hudson Valley

Find out more about Dover Plains

Dover Plains Holiday Homes information

Number of reviews
180
Accommodation
244 Holiday Homes
Lowest Price
€144
Highest Price
€3,077