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
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 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)
"Very nice, great location in town"
United States
Lisa F.
The price is HK$1,300
HK$1,652 total
includes taxes & fees
1 Oct - 2 Oct
Mid Century Modern Studio w/ Full Kitchen - Newly Built
A white house with a steeply pitched roof and a small tower-like structure.

2. 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, (7 reviews)
"Lovely home in the heart of Millbrook."
United States
Marianne A S.
The price is HK$2,510
HK$3,638 total
includes taxes & fees
28 Sept - 29 Sept
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
A rustic cabin surrounded by a forest with a stream in the foreground.

3. Creek Side Cabin with Wood Fired Hot Tub and Fire Pit

Creek Side Cabin with Wood Fired Hot Tub and Fire Pit
New Milford
10.0 out of 10, Exceptional, (3 reviews)
"Great little house, our favorite part was the gorgeous creek. Absolutely would recommend to pet lovers and those looking for peaceful nature :)"
United States
Kristine W.
The price is HK$2,425
HK$4,136 total
includes taxes & fees
29 Sept - 30 Sept
Creek Side Cabin with Wood Fired Hot Tub and Fire Pit
A spacious living room with a large wooden dining table, a comfortable sofa, and a bookshelf filled with books and decorative items.

4. 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$3,138
HK$6,185 total
includes taxes & fees
4 Oct - 5 Oct
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
A farm sign for Clover Brooke Farm in Hyde Park, NY, with a barn and a building in the background.

5. 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$1,723 total
includes taxes & fees
28 Sept - 29 Sept
Hudson Valley Farm Getaway- West/Llama Lover Lane
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

6. 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$635
HK$1,248 total
includes taxes & fees
13 Oct - 14 Oct
Cozy private room in a shared home with a Full-size bed and private bathroom.
A modern kitchen with white cabinets, a central island, and a view to the outside.

7. 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$882
HK$1,619 total
includes taxes & fees
28 Sept - 29 Sept
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
A modern living room with a sectional sofa, a coffee table, and a bar area with stools.

8. 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$988
HK$1,517 total
includes taxes & fees
28 Sept - 29 Sept
Private, Cozy, Clean apartment in lovely Hyde Park
A neatly made bed with a white pillow, a red pillow, and a white blanket. There is a small bedside table with a lamp.

9. Hibiscus Suite - Private Studio Apartment in Rhinebeck Village

Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
Rhinebeck Village
10.0 out of 10, Exceptional, (33 reviews)
"Beautiful place has a great stay!"
United States
Heather O.
The price is HK$861
HK$2,039 total
includes taxes & fees
29 Sept - 30 Sept
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
A house surrounded by a dense forest with a hammock and a small shed.

10. Enchanting Lake front chalet with backyard and fire pit. Dog friendly.

Enchanting Lake front chalet with backyard and fire pit. Dog friendly.
Carmel Hamlet
10.0 out of 10, Exceptional, (3 reviews)
"Great place, responsive host. Would return!"
United States
Brian S.
The price is HK$1,177
HK$2,338 total
includes taxes & fees
30 Sept - 1 Oct
Enchanting Lake front chalet with backyard and fire pit. Dog friendly.
A kitchen with wooden cabinets, a black countertop, a sink, and a window with a view of trees.

11. "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$4,233 total
includes taxes & fees
30 Sept - 1 Oct
"Country outside the city " 3 bedrooms 2 full bathrooms
A room with a bed, a couch, a desk with a computer, and various wall decorations.

12. 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 HK$1,663
HK$2,142 total
includes taxes & fees
29 Sept - 30 Sept
Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
A living room with a television, a cabinet, a glass coffee table, and a framed picture on the wall.

13. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Stanfordville
The price is HK$3,530
HK$5,147 total
includes taxes & fees
5 Oct - 6 Oct
Chic Lakeside Oasis|Near Rhinebeck & Millbrook
A picnic setup with a checkered blanket, a basket, and two wine glasses on a grassy area with a lake and trees in the background.

14. Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
New Fairfield
8.6 out of 10, Excellent, (36 reviews)
"Very serene location, the host was very responsive and helpful."
United States
Stephen L.
The price is HK$996
HK$2,656 total
includes taxes & fees
18 Oct - 19 Oct
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
A modern living room with a grey sofa, a wooden coffee table, and a staircase leading to an upper floor.

15. Chic Barn Style * Fireplace * Near Stissing House

Chic Barn Style * Fireplace * Near Stissing House
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$1,467
HK$5,022 total
includes taxes & fees
28 Sept - 29 Sept
Chic Barn Style * Fireplace * Near Stissing House
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

16. 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$1,326
HK$2,121 total
includes taxes & fees
28 Sept - 29 Sept
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
A compact room with a kitchenette, a bed, a wall decorated with photos and a mirror, and a 'No Fishing From Bridge' sign.

17. 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$1,445 total
includes taxes & fees
28 Sept - 29 Sept
Welcome to Sweet Abby Rose!
A deck with a red umbrella, wooden chairs, and a table with potted plants.

18. Mid-Century DJ’s Dream

Mid-Century DJ’s Dream
Staatsburg
10.0 out of 10, Exceptional, (59 reviews)
"Quiet clean accommodations in a central location for exploring the Hudson Valley."
United States
Alexandra R.
The price is HK$1,249
HK$1,945 total
includes taxes & fees
4 Oct - 5 Oct
Mid-Century DJ’s Dream
A modern kitchen with a granite countertop, a built-in stove, and a dining area with a glass table and chairs.

19. 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, (5 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 HK$1,260
HK$3,194 total
includes taxes & fees
28 Sept - 29 Sept
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
A spacious living room with a large window overlooking a lake, wooden ceiling, and comfortable seating.

20. Escape to Bantam Lake- With Fireplace and Hot tub!

Escape to Bantam Lake- With Fireplace and Hot tub!
Morris
10.0 out of 10, Exceptional, (4 reviews)
"This house is a dream. First, the views are incredible. Second, it’s beautifully decorated and very cozy. Lastly, the property location is perfect. I can’t wait to stay again!"
United States
Shannon M.
The price is HK$2,275
HK$4,212 total
includes taxes & fees
5 Oct - 6 Oct
Escape to Bantam Lake- With Fireplace and Hot tub!
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

SureStay Plus Hotel by Best Western Highland Poughkeepsie

SureStay Plus Hotel by Best Western Highland Poughkeepsie

8/10 Good
"This is a cost-effective option for the region. The rooms are clean, but the motel has a run-down feel to it. When we arrived, the card-key generator wasn't working. Staff let us in to our room, and we got working keys the next morning, but I haven't run into that problem anywhere else. Likewise, the card-reader on a side entrance, which would have been very useful for accessing our room, was broken, necessitating a longer walk around to the front of the motel. In the shower, the plate behind the dial had come away from the wall. It didn't affect the quality of the shower (which was fine in terms of heat and pressure), but it's not a good look. Breakfast was good and plentiful (I had scrambled eggs and sausages, but there's also cereal, various breads, and a waffle-maker, with orange and apple juice). My wife and I would come back, and thus the "Good" overall rating."
Robert 2-night trip
Posted less than an hour ago
SureStay Plus Hotel by Best Western Highland Poughkeepsie

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?

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: This holiday home rental outside of Dover Plains offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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 Bull's Bridge 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.