Dover Plains Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Dover Plains vacation 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
$161 nightly
The price is $183
Nov 6 - Nov 7
Total with taxes and fees
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, (9 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.
$415 nightly
The price is $469
Nov 8 - Nov 9
Total with taxes and fees
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
A spacious living room with a large wooden dining table, a comfortable sofa, and a bookshelf filled with books and decorative items.

3. 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, (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!"
United States
Beth E.
$673 nightly
The price is $761
Nov 10 - Nov 11
Total with taxes and fees
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
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
8.0 out of 10, Very good, (4 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.
$471 nightly
The price is $536
Nov 16 - Nov 17
Total with taxes and fees
Creek Side Cabin with Wood Fired Hot Tub and Fire Pit
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

5. 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.
$115 nightly
The price is $130
Nov 9 - Nov 10
Total with taxes and fees
Cozy private room in a shared home with a Full-size bed and private bathroom.
A residential property with a well-maintained lawn, a small house with a front porch, and a garage.

6. Sharon Retreat w/ Private Yard

Sharon Retreat w/ Private Yard
Sharon
9.2 out of 10, Wonderful, (37 reviews)
"Cagney’s home was so comfy! We loved the spacious family room. The beds were comfortable and the fully stocked kitchen made cooking much easier. Absolutely would love to stay at your cottage again!"
United States
Heidi F.
$407 nightly
The price is $464
Nov 6 - Nov 7
Total with taxes and fees
Sharon Retreat w/ Private Yard
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, (9 reviews)
"Great location not too far from the CIA."
United States
alexandra a.
$201 nightly
The price is $218
Dec 1 - Dec 2
Total with taxes and fees
Hudson Valley Farm Getaway- West/Llama Lover Lane
A wooden barrel structure with a door, two wooden lounge chairs, and a small table.

8. 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.
$506 nightly
The price is $576
Nov 10 - Nov 11
Total with taxes and fees
Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
A deck with a red umbrella, wooden chairs, and a table with potted plants.

9. Mid-Century DJ’s Dream

Mid-Century DJ’s Dream
Staatsburg
10.0 out of 10, Exceptional, (61 reviews)
"Quiet clean accommodations in a central location for exploring the Hudson Valley."
United States
Alexandra R.
$207 nightly
The price is $234
Nov 11 - Nov 12
Total with taxes and fees
Mid-Century DJ’s Dream
A modern kitchen with white cabinets, a central island, and a view to the outside.

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

Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
Staatsburg
9.6 out of 10, Exceptional, (13 reviews)
"We thoroughly enjoyed our stay. We would definitely come back! A fantastic location. And very good communication with the host, Alexander."
United States
elizabeth
$177 nightly
The price is $201
Nov 10 - Nov 11
Total with taxes and fees
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
A covered outdoor deck with wicker furniture, a grill, and a view of a lake.

11. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Stanfordville
$570 nightly
The price is $645
Nov 8 - Nov 9
Total with taxes and fees
Chic Lakeside Oasis|Near Rhinebeck & Millbrook
A farm sign for Clover Brooke Farm in Hyde Park, NY, with a barn and a building in the background.

12. 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.
$196 nightly
The price is $213
Nov 8 - Nov 9
Total with taxes and fees
Hudson Valley Farm Getaway-East/Alpaca Lane-Apt 1
A kitchen with wooden cabinets, a black countertop, a sink, and a window with a view of trees.

13. "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.
$464 nightly
The price is $525
Nov 11 - Nov 12
Total with taxes and fees
"Country outside the city " 3 bedrooms 2 full bathrooms
A hot tub in a backyard with a house, trees, and a clear sky.

14. Las Flores Villa

Las Flores Villa
5.0 star property
New Preston
10.0 out of 10, Exceptional, (1 review)
$1,343 nightly
The price is $1,544
Nov 6 - Nov 7
Total with taxes and fees
Las Flores Villa
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

15. 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.
$236 nightly
The price is $267
Nov 8 - Nov 9
Total with taxes and fees
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock 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.

16. 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.
$230 nightly
The price is $261
Nov 9 - Nov 10
Total with taxes and fees
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
A modern kitchen with a granite countertop, a built-in stove, and a dining area with a glass table and chairs.

17. Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Poughkeepsie
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!"
United States
Nicole Y.
$411 nightly
The price is $481
Nov 9 - Nov 10
Total with taxes and fees
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
A modern living room with a grey sofa, a wooden coffee table, and a staircase leading to an upper floor.

18. 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.
$628 nightly
The price is $704
Nov 9 - Nov 10
Total with taxes and fees
NEW: Chic Modern Barn Style Home in Fun Area
A large wooden dining table surrounded by chairs, with a stone fireplace and large windows in the background.

19. 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, (14 reviews)
"Clean, comfortable, private, and plenty of room. Hosts went above and beyond to make our stay easy and memorable."
United States
Polly J.
$1,120 nightly
The price is $1,267
Nov 6 - Nov 7
Total with taxes and fees
The George is an elegant restored home in the Hudson Valley
A cozy cabin interior with a wooden ceiling, a sofa, a coffee table, and a sign reading "Our Happy Place".

20. The Little Lake Cabin with hot tub

The Little Lake Cabin with hot tub
New Fairfield
10.0 out of 10, Exceptional, (6 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.
$462 nightly
The price is $527
Nov 8 - Nov 9
Total with taxes and fees
The Little Lake Cabin with 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

A living room with a fireplace, a piano, and a sofa.
The Kent Collection - The Firefly Inn

The Kent Collection - The Firefly Inn

The Kent Collection - The Firefly Inn
Kent

10/10 Excellent

Comfortable and friendly
United States
Helen
Reviewed October 29, 2026
The Kent Collection - The Firefly Inn

Find out more about Dover Plains

Everything you need to know about Dover Plains vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Dover Plains vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Dover Plains vacation 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 low season months. For more hustle and bustle, you may prefer to visit Dover Plains in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $91 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Dover Plains rentals

At Expedia, we put the best Dover Plains vacation 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 vacation.

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 vacation rentals in Dover Plains?

Yes, we give you a choice of vacation rentals close to well known local attractions 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 vacation rentals that Dover Plains has to offer?

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: This vacation home near Dover Plains offers a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals are there in Dover Plains?

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

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 larger area.

What’s a vacation rental in Dover Plains like?

A vacation rental is a private property you can book for short or long periods in Dover Plains. Vacation rentals offer amenities such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a clean environment, a vacation rental can offer a sense of safety away from public hotel elevators and busy lobbies while still allowing you to travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for families.

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