Dover Plains Vacations from $518

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The Latest Dover Plains vacation packages

Price found within the past 48 hours. Click for updated prices.
Radio Hotel

Radio Hotel

4 out of 5
Manhattan
Save 100% on your flight
Price was $1,016, price is now $518 per person
$518
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.6/10 Excellent! (2,498 reviews)
My room was not that clean at arrival, my shower pressure was very low I spoke to two different staff members to no avail. The drink vouchers was a hoax as they changed what 1 drink was voucher eligible in the middle of the day without notice. I was charged an amenity fee per day NO amenities, this place has potential but needs work.

Reviewed on Jul 14, 2026

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Price was $2,560, price is now $1,351 per person
$1,351
per person
Oct 4 - Oct 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.6/10 Exceptional! (1,617 reviews)
Staff was wonderful and friendly. Everything was very clean. Roof top patio was a plus with great views of the city, as was the close proximity to Little Italy and all its restaurants. Would definitely stay again. Did not use any of the amenities besides the free coffe which is why I gave that a 4.

Reviewed on Jul 13, 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was $1,694, price is now $935 per person
$935
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (3,130 reviews)
Clean, and friendly staff

Reviewed on Jul 13, 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was $1,602, price is now $891 per person
$891
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (3,652 reviews)
Check in and check out front desk staff wasn't friendly.

Reviewed on Jul 14, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was $2,892, price is now $1,608 per person
$1,608
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (1,006 reviews)
Lovely hotel in a great area

Reviewed on Jul 13, 2026

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Stay 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.
See properties

Dover Plains Hotel Deals

Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

3 out of 5
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
$109 nightly
The price is $127 total per night from Aug 9 to Aug 10
$127 total
Aug 9 - Aug 10
Total with taxes and fees
9/10 Wonderful! (1,023 reviews)
"Clean room and very spacious for double queen bed. Beds not as comfortable to sleep in but easier to get in than the typical high hotel bed. Staff was courteous and fulfilled request kindly. Overall not a bad experience."

Reviewed on Jul 13, 2026

Hyatt Place Poughkeepsie / Hudson Valley
Spark by Hilton Fishkill

Spark by Hilton Fishkill

3 out of 5
20 Schuyler Blvd Fishkill NY
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $103 total per night from Aug 2 to Aug 3
$103 total
Aug 2 - Aug 3
Total with taxes and fees
8.4/10 Very Good! (163 reviews)
"Dd"

Reviewed on Jul 10, 2026

Spark by Hilton Fishkill
SureStay Plus Hotel by Best Western Highland Poughkeepsie

SureStay Plus Hotel by Best Western Highland Poughkeepsie

2.5 out of 5
3423 US Highway 9W Highland NY
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $109 total per night from Jul 19 to Jul 20
$109 total
Jul 19 - Jul 20
Total with taxes and fees
8/10 Very Good! (1,014 reviews)
"Great for a lower cost place to stay without sacrificing everything. There is no gym, no pool, no elevator, and poor sound proofing. BUT, guests were respectful during quiet hours, the breakfast was decent, and the staff was helpful and pleasant."

Reviewed on Jul 13, 2026

SureStay Plus Hotel by Best Western Highland Poughkeepsie
See all 878 properties in Dover Plains
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 $518 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.