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Dover Plains Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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
10.0 out of 10, Exceptional, (24 reviews)
"Very nice, great location in town"
United States
Lisa F.
$186 nightly
The price is $211
Oct 1 - Oct 2
Total with taxes and fees
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
$141 nightly
The price is $159
Oct 13 - Oct 14
Total with taxes and fees
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)
"Lovely home in the heart of Millbrook."
United States
Marianne A S.
$410 nightly
The price is $464
Sep 27 - Sep 28
Total with taxes and fees
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
A wooden deck with a lounge chair and a table, a small wooden house with a door and windows, and a wooden fence.

4. Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.

Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.
Carmel
9.0 out of 10, Wonderful, (12 reviews)
"Such a lovely cabin - so many details to make for an incredible stay. Amazing location - lake, mountains! Wylda was wonderful."
United States
Clare
Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.
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.
$697 nightly
The price is $788
Oct 4 - Oct 5
Total with taxes and fees
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
A deck with a red umbrella, wooden chairs, and a table with potted plants.

6. 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.
$215 nightly
The price is $243
Sep 27 - Sep 28
Total with taxes and fees
Mid-Century DJ’s Dream
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-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.
$202 nightly
The price is $220
Sep 27 - Sep 28
Total with taxes and fees
Hudson Valley Farm Getaway-East/Alpaca Lane-Apt 1
A neatly made bed with a white pillow, a red pillow, and a white blanket. There is a small bedside table with a lamp.

8. 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 $260
Sep 29 - Sep 30
Total with taxes and fees
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
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.
$171 nightly
The price is $193
Sep 28 - Sep 29
Total with taxes and fees
Private, Cozy, Clean apartment in lovely Hyde Park
A modern living room with a grey sofa, a wooden coffee table, and a staircase leading to an upper floor.

10. 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.
$567 nightly
The price is $640
Sep 28 - Sep 29
Total with taxes and fees
Chic Barn Style * Fireplace * Near Stissing House
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.

11. 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.
$297 nightly
The price is $339
Oct 18 - Oct 19
Total with taxes and fees
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
A compact room with a kitchenette, a bed, a wall decorated with photos and a mirror, and a 'No Fishing From Bridge' sign.

12. 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.
$170 nightly
The price is $184
Sep 27 - Sep 28
Total with taxes and fees
Welcome to Sweet Abby Rose!
A modern kitchen with white cabinets, a central island, and a view to the outside.

13. 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.
$184 nightly
The price is $209
Sep 27 - Sep 28
Total with taxes and fees
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
A kitchen with wooden cabinets, a black countertop, a sink, and a window with a view of trees.

14. "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.
$477 nightly
The price is $540
Sep 30 - Oct 1
Total with taxes and fees
"Country outside the city " 3 bedrooms 2 full bathrooms
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.
$239 nightly
The price is $270
Sep 27 - Sep 28
Total with taxes and fees
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
A brick building with a sign reading 'Lobby' in front.

16. 2 Full Beds | Non-Smoking, Kitchen

2 Full Beds | Non-Smoking, Kitchen
Fishkill
9.2 out of 10, Wonderful, (21 reviews)
"great place tostay"
United States
Anonymous traveler
$88 nightly
The price is $102
Oct 22 - Oct 23
Total with taxes and fees
2 Full Beds | Non-Smoking, Kitchen
A hotel lobby with a reception desk, seating area, and a fire extinguisher on the wall.

17. 1 King Bed | Non-Smoking, Kitchen, Shower

1 King Bed | Non-Smoking, Kitchen, Shower
Fishkill
9.6 out of 10, Exceptional, (18 reviews)
"Great rooms and service,"
United States
Anonymous traveler
$72 nightly
The price is $82
Oct 19 - Oct 20
Total with taxes and fees
1 King Bed | Non-Smoking, Kitchen, Shower
A living room with a television, a cabinet, a glass coffee table, and a framed picture on the wall.

18. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Stanfordville
$578 nightly
The price is $654
Oct 1 - Oct 2
Total with taxes and fees
Chic Lakeside Oasis|Near Rhinebeck & Millbrook
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.
$348 nightly
The price is $407
Sep 28 - Sep 29
Total with taxes and fees
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
A spacious living room with a fireplace, a dining area with a view of a lake, and a cozy seating arrangement.

20. 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.
$357 nightly
The price is $387
Oct 5 - Oct 6
Total with taxes and fees
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
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

Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn

10/10 Excellent
"The bartender she is excellent"
vera alice 1-night trip
Posted less than an hour ago
Beekman Arms and Delamater 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 $93 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.

Explore a world of travel with Expedia

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.