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

Holiday Rentals in Dover Plains

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 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
9.8 out of 10, Exceptional, (26 reviews)
"Very private, rural spot. Immaculate, thoughtfully furnished, lacking nothing"
United States
benjamin
The price is €195
includes taxes & fees
13 Oct - 14 Oct
Mid Century Modern Studio w/ Full Kitchen - Newly Built
A spacious living room with a large wooden dining table, a comfortable sofa, and a bookshelf filled with books and decorative items.

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 €755
includes taxes & fees
18 Oct - 19 Oct
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
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, (8 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 €439
includes taxes & fees
12 Oct - 13 Oct
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.

4. 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 €507
includes taxes & fees
13 Oct - 14 Oct
Creek Side Cabin with Wood Fired Hot Tub and Fire Pit
A living room with a television, a cabinet, a glass coffee table, and a framed picture on the wall.

5. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Stanfordville
The price is €616
includes taxes & fees
12 Oct - 13 Oct
Chic Lakeside Oasis|Near Rhinebeck & Millbrook
A wooden barrel structure with a door, two wooden lounge chairs, and a small table.

6. 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.
The price is €544
includes taxes & fees
10 Nov - 11 Nov
Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
A farm sign for Clover Brooke Farm in Hyde Park, NY, with a barn and a building in the background.

7. 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 €206
includes taxes & fees
12 Oct - 13 Oct
Hudson Valley Farm Getaway- West/Llama Lover Lane
A room with a built-in bench along a wall with large windows, a door, and a tiled floor.

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 & Dining
New Milford
The price is €722
includes taxes & fees
14 Oct - 15 Oct
The Lorelai at Middle Street Manor: Walk to Town Green, Gazebo, Shops & Dining
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

9. 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."
United States
Jim B.
The price is €123
includes taxes & fees
13 Oct - 14 Oct
Cozy private room in a shared home with a Full-size bed and private bathroom.
A large wooden dining table surrounded by chairs, with a stone fireplace and large windows in the background.

10. The George is an elegant restored home in the Hudson Valley

The George is an elegant restored home in the Hudson Valley
Stanfordville
9.8 out of 10, Exceptional, (11 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 €995
includes taxes & fees
12 Oct - 13 Oct
The George is an elegant restored home in the Hudson Valley
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 €508
includes taxes & fees
13 Oct - 14 Oct
"Country outside the city " 3 bedrooms 2 full bathrooms
A modern kitchen with a granite countertop, a built-in stove, and a dining area with a glass table and chairs.

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, (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 €374
includes taxes & fees
13 Oct - 14 Oct
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
A hot tub in a backyard with a house, trees, and a clear sky.

13. Las Flores Villa

Las Flores Villa
5.0 star property
New Preston
10.0 out of 10, Exceptional, (1 review)
The price is €3,129
includes taxes & fees
13 Oct - 14 Oct
Las Flores Villa
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 €301
includes taxes & fees
18 Oct - 19 Oct
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
A modern kitchen with white cabinets, a large island, and a skylight.

15. 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)
"We loved the house and it really added to our upstate experience!!"
United States
stephen r.
The price is €1,195
includes taxes & fees
16 Oct - 17 Oct
A Country Lodge Straight Out of the Pages of a Great Novel
A spacious living room with a large window overlooking a lake, wooden ceiling, and comfortable seating.

16. 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, (5 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 €515
includes taxes & fees
2 Nov - 3 Nov
Escape to Bantam Lake- With Fireplace and Hot tub!
A cozy cabin interior with a wooden ceiling, a sofa, a coffee table, and a sign reading "Our Happy Place".

17. The Little Lake Cabin with hot tub

The Little Lake Cabin with hot tub
New Fairfield
10.0 out of 10, Exceptional, (4 reviews)
"Great location and lots to do despite it raining for half our stay! My dog enjoyed the yard and walks around the neighborhood. My son loved kayaking and having his first ever s’more. Honestly I wished we had booked a longer trip! "
United States
Lyndsey F.
The price is €508
includes taxes & fees
26 Oct - 27 Oct
The Little Lake Cabin with hot tub
A bedroom with a bed, a window, a heater, and a door leading to another room.

18. Hudson Valley Duplex: Hike, Sip + Explore!

Hudson Valley Duplex: Hike, Sip + Explore!
3.0 star property
Highland
Hudson Valley Duplex: Hike, Sip + Explore!
A farm sign for Clover Brooke Farm in Hyde Park, NY, with a barn and a building in the background.

19. Hudson Valley Farm Getaway-East/Alpaca Lane-Apt 1

Hudson Valley Farm Getaway-East/Alpaca Lane-Apt 1
Hyde Park
8.6 out of 10, Excellent, (4 reviews)
"Great spot if you’re looking for a quiet rural area ! Seeing the llamas made the stay more fun. We weren’t there when the store was open so it was a bit disappointing we couldn’t see more of what the farm offers. We’d definitely go again."
United States
Meg H.
The price is €218
includes taxes & fees
18 Oct - 19 Oct
Hudson Valley Farm Getaway-East/Alpaca Lane-Apt 1
A modern kitchen with white cabinets, a central island, and a view to the outside.

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

Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
Staatsburg
9.4 out of 10, Exceptional, (10 reviews)
"Nice stay for our quick overnight Comfortable space "
United States
jay c.
The price is €192
includes taxes & fees
19 Oct - 20 Oct
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Dover Plains Hotel Reviews

Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn

8/10 Good
"This was my first time at this property. My room was not in the Beekman Arms but in its sister property a few blocks away. The room was large and nicely decorated, it was very clean and the bed was comfortable. The bathroom was very nice and soap, shampoo and towels were supplied in abundance. Breakfast was included and consisted of all sorts of breads, fruit, yogurt, hard boiled eggs, juiced coffee and teas. This was served in a separate building near the residential building Our room was on the third floor so the lack of an elevator pushed my 94 year old body a bit. I would definitely come back to the Beeckman Arms but next time I’ll request a downstairs room."
Steven 1-night trip
Posted 6 hours ago
Beekman Arms and Delamater Inn

Find out more about Dover Plains

Everything you need to know about Dover Plains holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Dover Plains holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Dover Plains holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Dover Plains holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Dover Plains. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Dover Plains holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Dover Plains holiday rentals we have selected for you start as low as €82 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Dover Plains rentals

At Expedia, we put the best Dover Plains holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Dover Plains rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Dover Plains holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Dover Plains. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.