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

Dover Plains Holiday Rentals

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Dover Plains holiday rentals

A living room with a fireplace, two armchairs, a sofa, and a TV.

1. Mid Century Modern Studio w/ Full Kitchen - Newly Built

Mid Century Modern Studio w/ Full Kitchen - Newly Built
Kent
10.0 out of 10, Exceptional, (24 reviews)
"Clean, quiet, well stocked studio with everything we needed for our weekend in Kent. Very convenient to town. Highly recommend!"
United States
Joy P.
The price is HK$1,529
HK$1,900 total
includes taxes & fees
21 Sept - 22 Sept
Mid Century Modern Studio w/ Full Kitchen - Newly Built
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 HK$600
HK$1,208 total
includes taxes & fees
4 Oct - 5 Oct
Cozy private room in a shared home with a Full-size bed and private bathroom.
A white house with a steeply pitched roof and a small tower-like structure.

3. Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village

Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
Millbrook
9.8 out of 10, Exceptional, (6 reviews)
"We had a wonderful time at this property. It was quaint and clean and right in the middle of town near everything. Thank you, Tanya."
United States
Laurie F.
The price is HK$2,510
HK$3,726 total
includes taxes & fees
14 Sept - 15 Sept
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
A compact room with a kitchenette, a bed, a wall decorated with photos and a mirror, and a 'No Fishing From Bridge' sign.

4. Welcome to Sweet Abby Rose!

Welcome to Sweet Abby Rose!
Brewster
10.0 out of 10, Exceptional, (1 review)
"The place is super comfortable and has a great outdoor area for chatting; I would definitely like to come back and stay longer."
United States
Yasmin G.
The price is HK$784
HK$1,453 total
includes taxes & fees
14 Sept - 15 Sept
Welcome to Sweet Abby Rose!
A spacious living room with a large wooden dining table, a comfortable sofa, and a bookshelf filled with books and decorative items.

5. 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 HK$3,137
HK$6,592 total
includes taxes & fees
20 Sept - 21 Sept
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
A modern kitchen with white cabinets, a central island, and a view to the outside.

6. Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,

Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
Staatsburg
9.8 out of 10, Exceptional, (7 reviews)
"Nice stay for our quick overnight Comfortable space "
United States
jay c.
The price is HK$875
HK$1,620 total
includes taxes & fees
16 Sept - 17 Sept
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
A brick building with a sign reading 'Lobby' in front.

7. 1 Queen Bed | Non-Smoking, Kitchen

1 Queen Bed | Non-Smoking, Kitchen
Fishkill
9.6 out of 10, Exceptional, (18 reviews)
"Nice place to stay"
United States
Anonymous traveller
The price is HK$642
HK$742 total
includes taxes & fees
5 Oct - 6 Oct
1 Queen Bed | Non-Smoking, Kitchen
A farm sign for Clover Brooke Farm in Hyde Park, NY, with a barn and a building in the background.

8. Hudson Valley Farm Getaway- West/Llama Lover Lane

Hudson Valley Farm Getaway- West/Llama Lover Lane
Hyde Park
9.8 out of 10, Exceptional, (8 reviews)
"Great location not too far from the CIA."
United States
alexandra a.
The price is HK$1,351
HK$1,759 total
includes taxes & fees
14 Sept - 15 Sept
Hudson Valley Farm Getaway- West/Llama Lover Lane
A modern living room with a sectional sofa, a coffee table, and a bar area with stools.

9. Private, Cozy, Clean apartment in lovely Hyde Park

Private, Cozy, Clean apartment in lovely Hyde Park
Hyde Park
10.0 out of 10, Exceptional, (2 reviews)
"The host was great, the place was really nice and cozy. I would definitely stay here again!!! "
United States
Janet M.
The price is HK$1,059
HK$1,606 total
includes taxes & fees
15 Sept - 16 Sept
Private, Cozy, Clean apartment in lovely Hyde Park
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

10. 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 HK$1,325
HK$2,191 total
includes taxes & fees
20 Sept - 21 Sept
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
A wooden barrel structure with a door, two wooden lounge chairs, and a small table.

11. Peaceful Cabin with Sauna, Hot Tub & Cold Plunge

Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
Cornwall
10.0 out of 10, Exceptional, (6 reviews)
"This cabin is so cute we had a relaxing time , will return"
United States
Candice S.
Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
A kitchen with wooden cabinets, a black countertop, a sink, and a window with a view of trees.

12. "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 HK$1,553
HK$4,516 total
includes taxes & fees
14 Sept - 15 Sept
"Country outside the city " 3 bedrooms 2 full bathrooms
A deck with a red umbrella, wooden chairs, and a table with potted plants.

13. Mid-Century DJ’s Dream

Mid-Century DJ’s Dream
Staatsburg
10.0 out of 10, Exceptional, (58 reviews)
"Quiet clean accommodations in a central location for exploring the Hudson Valley."
United States
Alexandra R.
The price is HK$1,223
HK$1,987 total
includes taxes & fees
16 Sept - 17 Sept
Mid-Century DJ’s Dream

14. 2 Queen Beds | Non-Smoking, Kitchen

2 Queen Beds | Non-Smoking, Kitchen
Fishkill
8.6 out of 10, Excellent, (24 reviews)
"Worst hotel experience I have ever had. Grounds were unkept. No one was at the front desk when I first arrived. Waited 20 minutes for someone to arrive and had to leave for dinner. Came back to find out that they were overbooked."
United States
Glenn
The price is HK$642
HK$726 total
includes taxes & fees
5 Oct - 6 Oct
2 Queen Beds | Non-Smoking, Kitchen
A white house with a grey roof, a balcony with a blue umbrella, and a visible chimney.

15. The Perch in the Purchase -- Cozy, unique, and private

The Perch in the Purchase -- Cozy, unique, and private
Southbury
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful place. Very clean & welcoming "
United States
Chris
The price is HK$1,143
HK$1,811 total
includes taxes & fees
15 Sept - 16 Sept
The Perch in the Purchase -- Cozy, unique, and private
A spacious living room with a fireplace, a dining area with a view of a lake, and a cozy seating arrangement.

16. 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 HK$1,623
HK$3,136 total
includes taxes & fees
23 Sept - 24 Sept
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
A modern living room with a grey sofa, a wooden coffee table, and a staircase leading to an upper floor.

17. 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, (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 HK$1,536
HK$5,384 total
includes taxes & fees
15 Sept - 16 Sept
NEW: Chic Modern Barn Style Home in Fun Area
A covered outdoor deck with a grill, a chair, and a view of a lake and forest.

18. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Stanfordville
The price is HK$3,529
HK$5,323 total
includes taxes & fees
14 Sept - 15 Sept
Chic Lakeside Oasis|Near Rhinebeck & Millbrook
An aerial view of a lakeside property with a dock, a small building, and several outdoor seating areas.

19. Rustic Cabin in Fishkill!

Rustic Cabin in Fishkill!
Fishkill
10.0 out of 10, Exceptional, (5 reviews)
"Ideal cabin getaway. "
United States
Nadja E.
The price is HK$2,372
HK$3,581 total
includes taxes & fees
14 Sept - 15 Sept
Rustic Cabin in Fishkill!
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

Mayflower Inn & Spa, Auberge Collection

Mayflower Inn & Spa, Auberge Collection

10/10 Excellent
"Everything was perfect—the room, the service, the restaurant, the spa; everything was perfect. An unforgettable experience."
Moshe 2-night trip
Posted 6 hours ago
Mayflower Inn & Spa, Auberge Collection

Find out more about Dover Plains

Search for holiday rentals in Dover Plains on Expedia! You can easily find your home rentals, villas, holiday apartments in Dover Plains using one of the methods below:

  • View our selection of featured holiday rentals in Dover Plains
  • Use the map to find apartments and other holiday homes in the Dover Plains neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Dover Plains while they last

Look no further and take a look at our great range of rental properties in Dover Plains!

Frequently asked questions

Are there holiday rentals in Dover Plains?

Yes, there are holiday rentals close to the most popular sights in Dover Plains, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Dover Plains has to offer?

The Chicken Coop: This holiday home rental outside of Dover Plains is located in a rural location, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Dover Plains?

Choose from 5 Expedia holiday rentals in Dover Plains for a memorable holiday.

What’s there to see and do in Dover Plains?

While exploring the area, visit family-friendly sights like Mid-Hudson Civic Center, or get outside and enjoy nature at Dover Plains Stone Church. Dover Town Hall and Kent Falls State Park are a couple of places you'll find in the wider area.

What’s a holiday rental in Dover Plains like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Dover Plains. Holiday rentals feature amenities such as patios, hot tubs and fire pits so your stay will be comfortable. If you're concerned about a sanitised environment, a holiday rental can offer a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for family trips.