Dover Plains Vacations from $312

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The Latest Dover Plains vacation packages

Price found within the past 48 hours. Click for updated prices.
OYO Times Square

OYO Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was $586, price is now $312 per person
$312
per person
Apr 23 - Apr 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
7.2/10 Good! (1,617 reviews)
Easy process and great location. Room is good for you need for a stay while you’re in the city

Reviewed on Feb 1, 2026

Topping Rose House

Topping Rose House

4.5 out of 5
Price was $735, price is now $339 per person
$339
per person
Mar 6 - Mar 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (136 reviews)
Great rooms, staff and food

Reviewed on Sep 28, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $3,375, price is now $1,783 per person
$1,783
per person
Apr 9 - Apr 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
8.8/10 Excellent! (1,000 reviews)
The entire stay was exceptional! From the point of entry to departure 10/10

Reviewed on Jan 29, 2026

Sheraton New York Times Square Hotel

Sheraton New York Times Square Hotel

4 out of 5
Manhattan
Save 100% on your flight
Price was $645, price is now $345 per person
$345
per person
Mar 18 - Mar 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
7.4/10 Good! (5,413 reviews)
Room was nice, great location. Only issue was It took over an hour to get bath towels.

Reviewed on Feb 3, 2026

Mountain Springs Lake Resort

Mountain Springs Lake Resort

3.5 out of 5
Price was $727, price is now $403 per person
$403
per person
Mar 15 - Mar 19
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
9.6/10 Exceptional! (234 reviews)
The staff was friendly and helpful. They were great!

Reviewed on Feb 2, 2026

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Dover Plains Hotel Deals

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 Feb 16 to Feb 17
$119 total
Feb 16 - Feb 17
Total with taxes and fees
8.8/10 Excellent! (1,002 reviews)
Clean and good staff

Reviewed on Jan 27, 2026

Courtyard by Marriott Poughkeepsie
Hotel Zero Degrees Danbury

Hotel Zero Degrees Danbury

4 out of 5
15 Milestone Road Danbury CT
Fully refundableReserve now, pay when you stay
$159 nightly
The price is $183 total per night from Feb 22 to Feb 23
$183 total
Feb 22 - Feb 23
Total with taxes and fees
9/10 Wonderful! (1,004 reviews)
Excellent all around. Despite several birthday parties and a wedding in the restaurant the room was very quiet.

Reviewed on Feb 2, 2026

Hotel Zero Degrees Danbury
Inn at Bellefield / Hyde Park, Residence Inn by Marriott

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

3 out of 5
25 OLD VINEYARD PLACE Hyde Park NY
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $163 total per night from Feb 16 to Feb 17
$163 total
Feb 16 - Feb 17
Total with taxes and fees
9.6/10 Exceptional! (465 reviews)
The staff is incredibly courteous and helpful. The room is immaculate. Every amenity and convenience is considered in making your stay a pleasure.

Reviewed on Feb 1, 2026

Inn at Bellefield / Hyde Park, Residence Inn by Marriott
See all 851 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 $312 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.