Dover Plains Vacations from $884

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The Latest Dover Plains vacation packages

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

Hotel St. James

2.5 out of 5
Manhattan
Save 100% on your flight
Price was $1,536, price is now $884 per person
$884
per person
May 20 - May 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
8.8/10 Excellent! (7,024 reviews)
Super close to time square.

Reviewed on Mar 7, 2026

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Price was $1,774, price is now $931 per person
$931
per person
May 21 - May 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
9.6/10 Exceptional! (1,535 reviews)
Clean and well designed and finished. my favorite nyc hotel when i’m in need of a room that is mainly used to sleep between work days or full days of sight seeing.

Reviewed on Mar 5, 2026

The William Hotel Midtown, New York

The William Hotel Midtown, New York

2 out of 5
Manhattan
Save 100% on your flight
Price was $2,057, price is now $1,228 per person
$1,228
per person
May 20 - May 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
9.8/10 Exceptional! (31 reviews)
Cool room with a comfortable bed and a full kitchen very sweet staff. It’s close to the New York Public library, MOMA, Times Square, and more.

Reviewed on Mar 2, 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 $1,619, price is now $979 per person
$979
per person
May 14 - May 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,419 reviews)
Clean room, staff and breakfast

Reviewed on Mar 5, 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 $1,584, price is now $959 per person
$959
per person
May 14 - May 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (2,923 reviews)
Great location, clean, courteous staff, breakfast buffet had lots of options. Would definately stay again.

Reviewed on Mar 5, 2026

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Dover Plains Hotel Deals

Hotel Zero Degrees Danbury

Hotel Zero Degrees Danbury

4 out of 5
15 Milestone Road Danbury CT
Fully refundableReserve now, pay when you stay
$154 nightly
The price is $178 total per night from Mar 16 to Mar 17
$178 total
Mar 16 - Mar 17
Total with taxes and fees
9.2/10 Wonderful! (1,010 reviews)
Parking is easy and secure. Staff is amazing. Restaurant is right down stairs. Food is great! Kool hotel!

Reviewed on Mar 4, 2026

Hotel Zero Degrees Danbury
Courtyard by Marriott Poughkeepsie

Courtyard by Marriott Poughkeepsie

3 out of 5
2641 South Road/Route 9 Poughkeepsie NY
Fully refundableReserve now, pay when you stay
$105 nightly
The price is $119 total per night from Mar 23 to Mar 24
$119 total
Mar 23 - Mar 24
Total with taxes and fees
Courtyard by Marriott Poughkeepsie
Hampton Inn & Suites Poughkeepsie

Hampton Inn & Suites Poughkeepsie

2.5 out of 5
2361 South Rd Poughkeepsie NY
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $109 total per night from Mar 14 to Mar 15
$109 total
Mar 14 - Mar 15
Total with taxes and fees
9/10 Wonderful! (1,011 reviews)
Clean and staff very nice and helpful.

Reviewed on Mar 7, 2026

Hampton Inn & Suites Poughkeepsie
See all 846 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 $884 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.