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

Dover Plains Vacation Rentals

Dates

November 2026

December 2026

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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

Kent

benjamin

SAR 687 total

includes taxes & fees

9 Nov - 10 Nov

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

Millbrook

Laurie F.

SAR 1,762 total

includes taxes & fees

21 Nov - 22 Nov

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

Millbrook

Beth E.

SAR 2,981 total

includes taxes & fees

1 Dec - 2 Dec

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

New Milford

Kristine W.

SAR 2,014 total

includes taxes & fees

16 Nov - 17 Nov

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.

New Milford

Jim B.

SAR 490 total

includes taxes & fees

20 Nov - 21 Nov

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

Heidi F.

SAR 1,699 total

includes taxes & fees

9 Nov - 10 Nov

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

Hyde Park

alexandra a.

SAR 817 total

includes taxes & fees

1 Dec - 2 Dec

A wooden barrel structure with a door, two wooden lounge chairs, and a small table.

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

Cornwall

Candice S.

SAR 2,215 total

includes taxes & fees

10 Nov - 11 Nov

A deck with a red umbrella, wooden chairs, and a table with potted plants.

9. Mid-Century DJ’s Dream

Staatsburg

Alexandra R.

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,

Staatsburg

elizabeth

SAR 753 total

includes taxes & fees

1 Dec - 2 Dec

A covered outdoor deck with wicker furniture, a grill, and a view of a lake.

11. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Stanfordville

SAR 2,437 total

includes taxes & fees

1 Dec - 2 Dec

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

Hyde Park

Meg H.

SAR 817 total

includes taxes & fees

1 Dec - 2 Dec

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

Holmes

pamela w.

SAR 1,970 total

includes taxes & fees

11 Nov - 12 Nov

A hot tub in a backyard with a house, trees, and a clear sky.

14. Las Flores Villa

New Preston

SAR 5,367 total

includes taxes & fees

8 Nov - 9 Nov

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

Hopewell Junction

Peter W.

SAR 1,002 total

includes taxes & fees

8 Nov - 9 Nov

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

Rhinebeck Village

Heather O.

SAR 944 total

includes taxes & fees

10 Nov - 11 Nov

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

Poughkeepsie

Nicole Y.

SAR 1,826 total

includes taxes & fees

9 Nov - 10 Nov

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

Pine Plains

Estefany G.

SAR 2,644 total

includes taxes & fees

9 Nov - 10 Nov

A large, two-story house with a covered porch and a stone foundation, surrounded by snow-covered trees.

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

Stanfordville

Polly J.

SAR 4,756 total

includes taxes & fees

21 Nov - 22 Nov

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

New Fairfield

Lyndsey F.

SAR 1,978 total

includes taxes & fees

18 Nov - 19 Nov

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Find vacation rentals that suit your style

Top Dover Plains Hotel Reviews

A living room with a fireplace, a piano, and a sofa.

The Kent Collection - The Firefly Inn

Kent

10/10 Excellent

Helen

A hotel room with two beds, a desk, a chair, and a window with curtains.

Rocky River Inn

New Milford

10/10 Excellent

Zoe

A garden with a variety of plants and flowers, a white picket fence, and a small table with chairs.

Millbrook Country House Bed & Breakfast

Millbrook

10/10 Excellent

Anonymous traveler

A long dining table set for a meal with chairs, large windows, and a view of a park.

The Heartwood

Arlington

10/10 Excellent

Paulette

An outdoor seating area with stone walls, a fire feature, and yellow chairs.

Home2 Suites By Hilton Poughkeepsie

Poughkeepsie

10/10 Excellent

Comfy. Homey. Clean. Brightly lit and cheery lobby area. Great breakfast setup. Nice bedding. Spacious suite style. Easy and quick drive to Marist. Very small downers: Parking lot a tad cramped and narrow. Muddy construction lot in front. Desk staff tends to stray away from the desk and there was no telling when they would be back. Could use a desk sign or something saying "Back in 15 minutes."

David

A modern hotel with a prominent 'Hyatt Place' sign, outdoor seating area, and a covered entrance.

Hyatt Place Poughkeepsie / Hudson Valley

Crown Heights

10/10 Excellent

It was a special stay for us, Marist graduation weekend 2025. Unfortunately, there was a mixup with our reservation. The fabulous front desk staff did not let us down, Kat, Julia & Tianna went above & beyond to “fix” the situation quickly! In addition, Jason, the hotel manager made sure we were super comfortable & had an enjoyable weekend with our son! Hotel was super clean, comfortable & breakfast was great! I would highly recommend this well run Hyatt!

Richard

A multi-story hotel with a central entrance, stone pillars, and a brick facade.

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

Hyde Park

10/10 Excellent

Sheri

A spacious living room with hardwood floors, a large dining area, and a cozy seating area with a red sofa and matching cushions.

Homestead Inn

New Milford

10/10 Excellent

This is my second time staying at the Inn, and everytime that out do themselves from the time before. Gave me a call to see if there was anything special I may need prior to my arrival. Room is spotless, probably the cleanest room I have ever experience. Convenient to the New Milford Green, plenty of good places to eat. Very quiet and restful. I will be staying at the end at least once a month over the next year, Highly recommend!!!

Bob

A large white building with green shutters, a covered patio with red umbrellas, and a well-maintained garden.

Le Chambord at Curry Estate

Hopewell Junction

10/10 Excellent

Beautiful property ! Anyone looking for wedding venue, check this place out ! When I walked in the door I was greeted and welcomed! The inside had old charm with beautiful woodworking, dining area was so charming , with white table cloths , beautiful windows i just wanted to sit there all day with a hot chocolate or a cup of tea ! The bedroom looked like it was recently redone with some beautiful older pieces of furniture but was spotless! towels were nice and thick! The bed was very very...

ChrisL

A modern hotel lobby with wooden flooring, yellow chairs, a long dining table, and pendant lighting.

Hampton Inn & Suites Poughkeepsie

Crown Heights

10/10 Excellent

Connie

A hotel entrance with a brick facade, a glass door entrance, and a paved walkway.

Holiday Inn Express Poughkeepsie by IHG

Poughkeepsie

10/10 Excellent

Leslie

A hotel room with a large bed, two bedside tables with lamps, a headboard with a mirror, a window with curtains, and an air conditioning unit.

Roosevelt Inn of Hyde Park

Hyde Park

10/10 Excellent

Adele

A Courtyard by Marriott hotel with a modern design, large windows, and a well-maintained lawn.

Courtyard by Marriott Poughkeepsie

Poughkeepsie

10/10 Excellent

Catherine

A breakfast table with a teapot, milk, and a bagel, set against a brick wall with a framed picture above.

Inn at Pine Plains

Pine Plains

10/10 Excellent

Kevin

A building entrance with a covered porch, stone pillars, and a mailbox.

Quality Inn Hyde Park Poughkeepsie North

Hyde Park

10/10 Excellent

Marjorie

A spacious lobby with a high ceiling, a reception desk, a seating area with blue sofas and armchairs, and a visible Pepsi refrigerator.

Comfort Suites Fishkill near Interstate 84

Fishkill

10/10 Excellent

Scott

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.

Dover Plains Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Dover Plains vacation rentals

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

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

3. Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway

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

5. Cozy private room in a shared home with a Full-size bed and private bathroom.

6. Sharon Retreat w/ Private Yard

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

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

9. Mid-Century DJ’s Dream

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

11. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

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

13. "Country outside the city " 3 bedrooms 2 full bathrooms

14. Las Flores Villa

15. Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

16. Hibiscus Suite - Private Studio Apartment in Rhinebeck Village

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

18. NEW: Chic Modern Barn Style Home in Fun Area

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

20. The Little Lake Cabin with hot tub

Find vacation rentals that suit your style

Top Dover Plains Hotel Reviews

The Kent Collection - The Firefly Inn

10/10 Excellent

Frequently Asked Questions

Are there vacation rentals in Dover Plains?

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

How many vacation rentals are there in Dover Plains?

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

What’s a vacation rental in Dover Plains like?