A person standing on rocks by a flowing stream in a forested area.

Holiday Homes in Dover Plains

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Dover Plains holiday homes

Interior

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 AU$1,156
includes taxes & fees
23 Aug - 24 Aug
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
Exterior

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

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.2 out of 10, Wonderful, (12 reviews)
"Lovely space and situation, unique. Close to the AT, as well."
United States
Peter W.
The price is AU$284
includes taxes & fees
18 Aug - 19 Aug
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Paper towels

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

Amazing 3-bedroom house with AC in adorable Highland
Highland
The price is AU$699
includes taxes & fees
9 Sept - 10 Sept
Amazing 3-bedroom house with AC in adorable Highland
Coffee/tea maker, fridge, microwave, oven

4. "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 AU$794
includes taxes & fees
15 Sept - 16 Sept
"Country outside the city " 3 bedrooms 2 full bathrooms
Interior

5. 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 AU$288
includes taxes & fees
14 Sept - 15 Sept
Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
TV, fireplace, books

6. NEW: Chic Modern Barn Style Home in Fun Area

NEW: Chic Modern Barn Style Home in Fun Area
Pine Plains
10.0 out of 10, Exceptional, (2 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 AU$1,061
includes taxes & fees
19 Aug - 20 Aug
NEW: Chic Modern Barn Style Home in Fun Area
TV, fireplace

7. 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, (18 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is AU$685
includes taxes & fees
10 Sept - 11 Sept
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Outdoor dining

8. 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, (73 reviews)
"Great spot! Very unique, has lots of charm!"
United States
Brian
The price is AU$457
includes taxes & fees
19 Aug - 20 Aug
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Living area

9. Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County

Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
Red Hook
10.0 out of 10, Exceptional, (26 reviews)
"It was pet friendly, even for a dog, was comfortable for the entire family and is a great location with easy access to surrounding villages."
United States
Susan T.
The price is AU$616
includes taxes & fees
23 Aug - 24 Aug
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
Cookware/dishes/utensils

10. Awesome Lake Home with tons of fun!

Awesome Lake Home with tons of fun!
New Fairfield
9.8 out of 10, Exceptional, (11 reviews)
"Nicole is a wonderful host. We had a fantastic stay at her house. The home was beautifully prepared, and we felt very comfortable throughout our visit. Even though it was a rainy weekend, we were still able to enjoy the huge hot tub and had a great time playing the card games and board games provided. Thank you!!"
United States
W Y.
The price is AU$1,014
includes taxes & fees
23 Aug - 24 Aug
Awesome Lake Home with tons of fun!
Interior

11. 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, (4 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 AU$864
includes taxes & fees
14 Sept - 15 Sept
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Dining

12. 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, (8 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 AU$1,516
includes taxes & fees
18 Aug - 19 Aug
The George is an elegant restored home in the Hudson Valley
Interior

13. rural, serene + sophisticated space

rural, serene + sophisticated space
Red Hook
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful property with unique accommodations in the Hudson Valley"
United States
BRIAN PATRICK M.
The price is AU$523
includes taxes & fees
30 Aug - 31 Aug
rural, serene + sophisticated space
Coffee/tea maker, fridge, microwave, oven

14. 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)
"Our group of parents and riders had a great stay during the Millbrook Horse Trials in July. Clean facility, ample room, responsive host. Would stay again."
United States
Hessie S.
The price is AU$2,020
includes taxes & fees
18 Aug - 19 Aug
A Country Lodge Straight Out of the Pages of a Great Novel
Exterior

15. 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 AU$1,005
includes taxes & fees
18 Aug - 19 Aug
Chestnut on Willow Lake
Smart TV, fireplace, video games, DVD player

16. Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.

Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.
Carmel Hamlet
10.0 out of 10, Exceptional, (21 reviews)
"Place was beautifully done, it’s obvious they take care of their place. The hosts were thoughtful and attentive, will definitely visit again. "
United States
Jasmine G.
The price is AU$1,419
includes taxes & fees
19 Aug - 20 Aug
Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.
Outdoor dining

17. Candlewood Lake Retreat with Private Dock

Candlewood Lake Retreat with Private Dock
New Milford
10.0 out of 10, Exceptional, (58 reviews)
"Great property for a family to enjoy the lake!"
United States
Jenny B.
The price is AU$2,998
includes taxes & fees
25 Aug - 26 Aug
Candlewood Lake Retreat with Private Dock
Property grounds

18. Red Cottage - Lakeside Property!

Red Cottage - Lakeside Property!
Fishkill
The price is AU$1,055
includes taxes & fees
18 Aug - 19 Aug
Red Cottage - Lakeside Property!
Exterior

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 AU$1,096
includes taxes & fees
18 Aug - 19 Aug
Hickory on Willow Lake
Private kitchen

20. 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
The price is AU$206
includes taxes & fees
1 Sept - 2 Sept
Cozy private room in a shared home with a Full-size bed and private bathroom.
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Dover Plains Hotel Reviews

Best Western Fishkill Inn & Suites

Best Western Fishkill Inn & Suites

10/10 Excellent
"Breakfast was good. Room was clean."
Hugo 2-night trip
Posted less than an hour ago
Best Western Fishkill Inn & Suites

Find out more about Dover Plains

Dover Plains Holiday Homes information

Number of reviews
Accommodation
 Holiday Homes
Lowest Price
Highest Price