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Holiday Homes in Dover Plains

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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 €740
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)
"The chapel was just as it was pictured. It has been beautifully restored. It was a very unique experience."
United States
Stella
The price is €178
includes taxes & fees
16 Aug - 17 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 €439
includes taxes & fees
17 Aug - 18 Aug
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 €510
includes taxes & fees
25 Aug - 26 Aug
"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 €182
includes taxes & fees
13 Sept - 14 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 €631
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 €439
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 €279
includes taxes & fees
16 Aug - 17 Aug
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Outdoor spa tub

9. Bespoke Litchfield - Family Friendly, Hot Tub

Bespoke Litchfield - Family Friendly, Hot Tub
Litchfield
10.0 out of 10, Exceptional, (2 reviews)
"This is a phenomenal location, the house is unparalleled. The host is amazing, friendly, informative, transparent. The house is very well appointed and well cared for. "
United States
Matt S.
The price is €893
includes taxes & fees
18 Aug - 19 Aug
Bespoke Litchfield - Family Friendly, Hot Tub
Living area

10. 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.
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
Cookware/dishes/utensils

11. 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 €621
includes taxes & fees
17 Aug - 18 Aug
Awesome Lake Home with tons of fun!
Interior

12. 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 €563
includes taxes & fees
17 Aug - 18 Aug
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Dining

13. 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 €966
includes taxes & fees
17 Aug - 18 Aug
The George is an elegant restored home in the Hudson Valley
Interior

14. 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 €328
includes taxes & fees
30 Aug - 31 Aug
rural, serene + sophisticated space
Exterior

15. 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 €681
includes taxes & fees
17 Aug - 18 Aug
Hickory on Willow Lake
Coffee/tea maker, fridge, microwave, oven

16. 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 €1,260
includes taxes & fees
17 Aug - 18 Aug
A Country Lodge Straight Out of the Pages of a Great Novel
Smart TV, fireplace, video games, DVD player

17. 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 €911
includes taxes & fees
18 Aug - 19 Aug
Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.
Outdoor dining

18. Candlewood Lake Retreat with Private Dock

Candlewood Lake Retreat with Private Dock
New Milford
10.0 out of 10, Exceptional, (57 reviews)
"Great property for a family to enjoy the lake!"
United States
Jenny B.
The price is €1,960
includes taxes & fees
25 Aug - 26 Aug
Candlewood Lake Retreat with Private Dock
Property grounds

19. Red Cottage - Lakeside Property!

Red Cottage - Lakeside Property!
Fishkill
The price is €646
includes taxes & fees
17 Aug - 18 Aug
Red Cottage - Lakeside Property!
Exterior

20. 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 €617
includes taxes & fees
17 Aug - 18 Aug
Chestnut 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

DoubleTree by Hilton Poughkeepsie Convention Center

DoubleTree by Hilton Poughkeepsie Convention Center

10/10 Excellent
"Well"
CYNTHIA 1-night trip
Posted 3 hours ago
DoubleTree by Hilton Poughkeepsie Convention Center

Find out more about Dover Plains

Dover Plains Holiday Homes information

Number of reviews
279
Accommodation
286 Holiday Homes
Lowest Price
€178
Highest Price
€1,960