Dover Plains Vacations from $219

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The Latest Dover Plains vacation packages

Price found within the past 48 hours. Click for updated prices.
Sheraton New York Times Square Hotel

Sheraton New York Times Square Hotel

4 out of 5
Manhattan
Price was $434, price is now $219 per person
$219
per person
Feb 6 - Feb 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
7.4/10 Good! (5,413 reviews)
Room had some wear and tear. Staff were fone

Reviewed on Nov 26, 2025

Radio Hotel

Radio Hotel

4 out of 5
Manhattan
Price was $661, price is now $322 per person
$322
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
8.6/10 Excellent! (2,613 reviews)
The location was ideal for our stay. The restaurant food was amazing.

Reviewed on Nov 22, 2025

Hilton Garden Inn Westchester Dobbs Ferry, NY

Hilton Garden Inn Westchester Dobbs Ferry, NY

3 out of 5
Price was $458, price is now $229 per person
$229
per person
Jan 30 - Feb 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
8.4/10 Very Good! (1,001 reviews)
Beautiful place to be

Reviewed on Nov 20, 2025

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was $600, price is now $306 per person
$306
per person
Feb 6 - Feb 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
9.2/10 Wonderful! (3,348 reviews)
Staff helpful and friendly. The room was clean , a nice size and a fab view.

Reviewed on Nov 26, 2025

Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Manhattan
Price was $1,269, price is now $664 per person
$664
per person
Feb 6 - Feb 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
9/10 Wonderful! (1,002 reviews)
helpful staff, nice rooms, location

Reviewed on Nov 24, 2025

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Dover Plains Hotel Deals

Quality Inn Poughkeepsie

Quality Inn Poughkeepsie

2.5 out of 5
536 Haight Ave, Building A Poughkeepsie NY
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $101 total per night from Dec 28 to Dec 29
$101 total
Dec 28 - Dec 29
Total with taxes and fees
7.6/10 Good! (488 reviews)
Best stay!

Reviewed on Nov 20, 2025

Quality Inn 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
$99 nightly
The price is $115 total per night from Dec 5 to Dec 6
$115 total
Dec 5 - Dec 6
Total with taxes and fees
8.8/10 Excellent! (1,006 reviews)
Spotless room

Reviewed on Nov 24, 2025

Hampton Inn & Suites 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
$160 nightly
The price is $184 total per night from Dec 20 to Dec 21
$184 total
Dec 20 - Dec 21
Total with taxes and fees
9/10 Wonderful! (1,000 reviews)
facility was immaculate and staff super professional. The culture could not have been better.

Reviewed on Nov 17, 2025

Hotel Zero Degrees Danbury
See all 862 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 $219 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.