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Our top choices for Dover Plains holiday homes
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
10.0 out of 10, Exceptional, (3 reviews)
"I really enjoyed my four night stay here."
Jim B.
The price is €119
includes taxes & fees
20 Nov - 21 Nov
2. Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
Steps to the Delightful Village of Millbrook ☆ Fun Family GetawayMillbrook
10.0 out of 10, Exceptional, (8 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!"
Beth E.
The price is €712
includes taxes & fees
15 Nov - 16 Nov
3. Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Chic Lakeside Oasis|Near Rhinebeck & MillbrookStanfordville
The price is €597
includes taxes & fees
12 Nov - 13 Nov
4. "Country outside the city " 3 bedrooms 2 full bathrooms
"Country outside the city " 3 bedrooms 2 full bathroomsHolmes
9.6 out of 10, Exceptional, (5 reviews)
"Great house! We had a fantastic weekend!! Thank you so much "
pamela w.
The price is €484
includes taxes & fees
15 Nov - 16 Nov
5. Las Flores Villa
Las Flores VillaNew Preston
10.0 out of 10, Exceptional, (1 review)
The price is €1,274
includes taxes & fees
12 Nov - 13 Nov
6. Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock ParkHopewell Junction
9.4 out of 10, Exceptional, (13 reviews)
"Lovely space and situation, unique. Close to the AT, as well."
Peter W.
The price is €230
includes taxes & fees
24 Nov - 25 Nov
7. The George is an elegant restored home in the Hudson Valley
The George is an elegant restored home in the Hudson ValleyStanfordville
9.8 out of 10, Exceptional, (15 reviews)
"Clean, comfortable, private, and plenty of room. Hosts went above and beyond to make our stay easy and memorable."
Polly J.
The price is €1,112
includes taxes & fees
12 Nov - 13 Nov
8. 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 & DiningNew Milford
10.0 out of 10, Exceptional, (2 reviews)
"The house was perfect for our girls weekend. It was even nicer in person."
Lauren B.
The price is €710
includes taxes & fees
12 Nov - 13 Nov
9. Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NYPoughkeepsie
9.8 out of 10, Exceptional, (6 reviews)
"Beautiful property with ample space for parking. Host was super nice and met all of our needs!"
Nicole Y.
The price is €419
includes taxes & fees
16 Nov - 17 Nov
10. 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
10.0 out of 10, Exceptional, (21 reviews)
"Beautiful house. Great location and awesome hosts!"
Robert T.
The price is €299
includes taxes & fees
12 Nov - 13 Nov
11. NEW: Chic Modern Barn Style Home in Fun Area
NEW: Chic Modern Barn Style Home in Fun AreaPine 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!"
Estefany G.
The price is €660
includes taxes & fees
12 Nov - 13 Nov
12. A Country Lodge Straight Out of the Pages of a Great Novel
A Country Lodge Straight Out of the Pages of a Great NovelPine Plains
10.0 out of 10, Exceptional, (15 reviews)
"Stayed with a group for Millbrook Horse Trials, we had an amazing weekend at this calm and relaxing home with plenty of beds and amenities! What a treat!"
Marianne R.
The price is €1,238
includes taxes & fees
12 Nov - 13 Nov
13. rural, serene + sophisticated space
rural, serene + sophisticated spaceRed Hook
10.0 out of 10, Exceptional, (9 reviews)
"Beautiful property with unique accommodations in the Hudson Valley"
BRIAN PATRICK M.
The price is €347
includes taxes & fees
1 Dec - 2 Dec
14. Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Large Relaxing Family Retreat In The Hudson Valley with Theatre and GazeboFishkill
9.2 out of 10, Wonderful, (81 reviews)
"The property was as advertised and met our needs for our trip."
Sara
The price is €292
includes taxes & fees
15 Nov - 16 Nov
15. Red Cottage - Lakeside Property!
Red Cottage - Lakeside Property!Fishkill
The price is €344
includes taxes & fees
12 Dec - 13 Dec
16. Chestnut on Willow Lake
Chestnut on Willow LakeFishkill
9.8 out of 10, Exceptional, (6 reviews)
"Our family enjoyed a relaxing weekend before R-day at West Point and it was perfect! A beautiful property and we hope to be back another time!"
Quintina R.
The price is €472
includes taxes & fees
12 Nov - 13 Nov
17. Hickory on Willow Lake
Hickory on Willow LakeFishkill
9.8 out of 10, Exceptional, (6 reviews)
"Clean, quiet and great location. Beautiful property."
Sheila B.
The price is €476
includes taxes & fees
12 Nov - 13 Nov
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.
Learn more about Dover Plains
Hikers find serenity on the Appalachian Trail that passes near this charming Hudson Valley town. Explore the natural beauty of Dover Stone Church, a cave with a waterfall that's perfect for summer adventures.
