Dover Plains Vacations from $663
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The Latest Dover Plains vacation packages
Price found within the past 48 hours. Click for updated prices.
33 Hotel, New York City, Seaport
Manhattan
$699
per person
Oct 24 - Oct 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (1,002 reviews)
Best staff at a hotel that I’ve ever met! So friendly and so many recommendations! Very nice rooms and bar area!! Amazing overall!
Reviewed on Sep 9, 2026
Seven Beach Lane
$793
per person
Oct 22 - Oct 27
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
9.4/10 Exceptional! (34 reviews)
Terrific first stay for our anniversary, and we will be back!
Jen and Kevin so sweet, helpful, and kind. Grounds are beautiful, rooms a bit small but pretty.
Watched Open in lobby late night, felt like we were home w a bigger TV.
Definite classy gem in Westhampton.
Reviewed on Sep 8, 2026
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See all available trips from Columbus to Dover Plains
View all tripsStay near popular Dover Plains attractions
Dover Plains Stone Church
A natural cavern with a 30-foot waterfall cascading through its gothic cathedral-like entrance. Hike the serene tree-lined path along Stone Church Brook to experience this geological wonder up close.
Dover Town Hall
Dover Town Hall serves as the administrative hub for municipal services in the Town of Dover. Visit during business hours to attend public meetings and gain insight into local governance.
Dover Plains Hotel Deals
Beekman Arms and Delamater Inn
6387 MILL ST Rhinebeck NY
Fully refundableReserve now, pay when you stay
$152 nightly
$172 total
Sep 14 - Sep 15
Total with taxes and fees
8.2/10 Very Good! (1,002 reviews)
"Awesome location and historic inn. Very interesting experience"
Reviewed on Sep 10, 2026
Holiday Inn Express Poughkeepsie by IHG
2750 South Road Poughkeepsie NY
Fully refundable
$100 nightly
$116 total
Sep 28 - Sep 29
Total with taxes and fees
8.8/10 Excellent! (1,002 reviews)
"Room was clean and comfortable. Breakfast was good and coffee was available 24rs a day in the lobby"
Reviewed on Sep 10, 2026
Hyatt Place Poughkeepsie / Hudson Valley
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
$97 nightly
$113 total
Sep 20 - Sep 21
Total with taxes and fees
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.
Find the Best Dover Plains Vacation Packages
Dover Plains Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 1,300 |
Max Temp Winter | 35ºF |
Max Temp Summer | 80ºF |
Top Sights | Millbrook Vineyards and Winery, Wings Castle and James Baird State Park |
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Frequently asked questions
How much does a Dover Plains vacation package cost?
You'll find cheap prices from $663 on Expedia for your Dover Plains break. However, a range of factors like the length of stay, hotel choice and season will influence how much your vacation to Dover Plains costs.
What are the cheapest months to go to Dover Plains?
December, January and February are the best times to search for cheap Dover Plains vacation packages. Choosing to travel in less busy months means you'll typically find lower prices on hotels and flights.
How many days is enough for Dover Plains?
The ideal length of your Dover Plains vacation depends on what you'd like to see. Typically, a handful of days to a week will give you plenty of time to check out all the major sights and discover some hidden gems along the way.
How to find the best Dover Plains package deals?
Start your search for a Dover Plains package deal by entering your destination and preferred travel dates under our "Packages" tab. Then select some filters, like "Popular locations" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the ideal Dover Plains package deal straight away, simply switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Dover Plains escape underway.
Is it cheaper to book a Dover Plains vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll typically snag a better deal than booking each component individually. And you'll still have the freedom to create a personalized Dover Plains vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Dover Plains?
If you're planning a spur-of-the-moment Dover Plains adventure, browse our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can score amazing deals on your flights and hotels by booking well in advance.
Does Expedia offer Book Now, Pay Later Dover Plains vacation packages?
Your Dover Plains trip is meant to be a relaxing escape from your busy life, not a source of money-related stress. So to give you a bit more flexibility, we've teamed up with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.
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- Vanderbilt Mansion National Historic Site
- Saint Vladimir's Orthodox Theological Seminary
- Omega Institute
- Home of Franklin D. Roosevelt National Historic Site
- Tuckahoe Vacations
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- Orvis Sandanona Shooting Grounds
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- Thunder Ridge Ski Resort
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- Hopewell Junction Vacations
- Visit Rhinebeck
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- Science Barge
- Whaley Lake
- Eleanor Roosevelt National Historic Site
- Crooked Island Caves
- Iona College
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- Trevor Zoo
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- Franklin D. Roosevelt Presidential Library and Museum
- Richard L. Skimin Memorial Baseball Field
- Philipse Manor Hall State Historic Site
- Sarah Lawrence College
- New Roc City
- Tibbetts Brook Park
- Lenoir Preserve
- Edward J. Murray Memorial Skating Center
- Vassar College
- Westchester Hills Cemetery
- Visit Dover Plains
- Poughkeepsie Vacations
- Newyork-Presbyterian - Westchester Hospital
- Patterson Vacations
- Hudson River Museum
- Innisfree Garden
- Clinton House State Historic Site
- James Baird State Park
- Culinary Institute of America
- Pleasant Valley Vacations
- Palisades Vacations
- Harlem Valley Rail Trail
- East Fishkill Community Library
- Clinton Corners Vacations
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- Splashdown Beach
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.