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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Dover Plains vacation homes

Private kitchen

1. 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 ￥10,834
￥22,974 total
includes taxes & fees
Sep 1 - Sep 2
Cozy private room in a shared home with a Full-size bed and private bathroom.
Interior

2. 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 ￥63,728
￥132,471 total
includes taxes & fees
Aug 23 - Aug 24
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
Exterior

3. 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 ￥16,729
￥32,081 total
includes taxes & fees
Aug 19 - Aug 20
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
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 ￥32,549
￥93,594 total
includes taxes & fees
Sep 16 - Sep 17
"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 ￥22,942
￥31,772 total
includes taxes & fees
Sep 16 - Sep 17
Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
Paper towels

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

Amazing 3-bedroom house with AC in adorable Highland
Highland
The price is ￥33,409
￥78,460 total
includes taxes & fees
Aug 31 - Sep 1
Amazing 3-bedroom house with AC in adorable Highland
TV, fireplace, books

7. 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 ￥37,504
￥116,767 total
includes taxes & fees
Aug 19 - Aug 20
NEW: Chic Modern Barn Style Home in Fun Area
TV, fireplace

8. 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, (19 reviews)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is ￥39,830
￥73,037 total
includes taxes & fees
Sep 17 - Sep 18
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Outdoor dining

9. 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 ￥39,432
￥52,227 total
includes taxes & fees
Aug 19 - Aug 20
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
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 ￥64,525
￥114,273 total
includes taxes & fees
Aug 23 - Aug 24
Awesome Lake Home with tons of fun!
Exterior

11. Family home by Polo fields with great yard & game rm. EV charger, pet friendly!

Family home by Polo fields with great yard & game rm. EV charger, pet friendly!
Pine Plains
10.0 out of 10, Exceptional, (7 reviews)
"It felt clean, comfortable, accomodating, and most important, safe. Our family had an amazing time here and we will definitely visit again. Thank you!"
United States
Jon W.
The price is ￥60,223
￥129,408 total
includes taxes & fees
Aug 26 - Aug 27
Family home by Polo fields with great yard & game rm. EV charger, pet friendly!
Living area

12. 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, (27 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 ￥39,432
￥71,643 total
includes taxes & fees
Aug 23 - Aug 24
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
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 ￥47,637
￥59,956 total
includes taxes & fees
Aug 30 - Aug 31
rural, serene + sophisticated space
Interior

14. 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 ￥50,512
￥102,642 total
includes taxes & fees
Aug 19 - Aug 20
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Dining

15. 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 ￥114,710
￥174,283 total
includes taxes & fees
Aug 19 - Aug 20
The George is an elegant restored home in the Hudson Valley
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 ￥141,795
￥234,663 total
includes taxes & fees
Aug 24 - Aug 25
A Country Lodge Straight Out of the Pages of a Great Novel
Exterior

17. 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 ￥78,863
￥113,391 total
includes taxes & fees
Aug 19 - Aug 20
Chestnut on Willow Lake
Outdoor dining

18. 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 ￥165,409
￥285,892 total
includes taxes & fees
Sep 17 - Sep 18
Candlewood Lake Retreat with Private Dock
Smart TV, fireplace, video games, DVD player

19. 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 ￥95,433
￥165,411 total
includes taxes & fees
Aug 25 - Aug 26
Beautiful Escape! Hudson Valley House. 90min from NYC & 30min from Beacon.
Property grounds

20. Red Cottage - Lakeside Property!

Red Cottage - Lakeside Property!
Fishkill
The price is ￥83,245
￥119,146 total
includes taxes & fees
Aug 19 - Aug 20
Red Cottage - Lakeside Property!
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

Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn

8/10 Good
"The Beekman Arms is a beautiful, historic hotel, and there is much to like about it. However, be warned: There is no elevator, and in its several buildings, the stairs are steep. Also be warned: the complementary breakfast is served in only one of the buildings (not the main one), and a walk of a block or two, depending on where you are staying, may be necessary, at times in the rain. On our second day there, the breakfast was disappointing, with the variety of breads and pastries present on our first day replaced by only one kind of bread and a soft roll. There were also no herbal teas available and only one variety of instant oatmeal. Our room on the second floor of the main house was charming but tiny, taken up mostly by a four-poster bed that, for my wife, was about chest high. The stool provided to enable her to get into it was helpful, but some might be put off. The huge, thick mattress was, however, quite comfortable. We got an unusually good rate on the room, due (according to the hotel) to the 250th anniversary year of the U.S. I would say it is questionable whether, with all its quirks and the tiny room, our stay would have been worth the higher, usual rate. But it was interesting to stay at an historic site decorated with authentic memorabilia of its illustrious past."
Nicholas 2-night trip
Posted 1 hour ago
Beekman Arms and Delamater Inn

Find out more about Dover Plains

Dover Plains Vacation Homes information

Number of reviews
7,207
Accommodation
257 Vacation Homes
Lowest Price
￥15,036
Highest Price
￥52,783