Dover Plains Vacations from $385

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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 $640, price is now $385 per person
$385
per person
May 27 - May 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
8.8/10 Excellent! (7,024 reviews)
Superb location. Room was clean. Staff friendly. Booked a king bed room and it was quite spacious for New York. Great budget hotel.

Reviewed on Mar 12, 2026

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Save 100% on your flight
Price was $3,784, price is now $2,224 per person
$2,224
per person
May 16 - May 23
just found
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,003 reviews)
Spotless property and extremely friendly staff! Would definitely stay here again!

Reviewed on Mar 1, 2026

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Price was $4,198, price is now $2,520 per person
$2,520
per person
Apr 29 - May 6
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to New Haven (HVN)
No reviews
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was $1,833, price is now $1,105 per person
$1,105
per person
May 23 - May 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,419 reviews)
The room was very clean and the staff were friendly. Breakfast was amazing every morning with a variety of selections. Will definitely stay here again.

Reviewed on Mar 12, 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 $1,533, price is now $928 per person
$928
per person
Apr 26 - May 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
7.4/10 Good! (7,063 reviews)
There were shops nearby, walking distances to a lot of the attractions

Reviewed on Mar 12, 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 Apr 12 to Apr 13
$178 total
Apr 12 - Apr 13
Total with taxes and fees
9.2/10 Wonderful! (1,001 reviews)
Second time staying at this hotel and second great experience. Clean, comfortable, easy parking, and good location right off the highway.

Reviewed on Mar 9, 2026

Hotel Zero Degrees Danbury
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 20 to Mar 21
$109 total
Mar 20 - Mar 21
Total with taxes and fees
9/10 Wonderful! (1,000 reviews)
We found a bug in our bed. Using Google image it was identified as a bed bug. We went to the front desk and they relocated us to a different floor and upgraded us to a suite. It left us uneasy but we were happy the staff took us seriously.

Reviewed on Mar 10, 2026

Hampton Inn & Suites Poughkeepsie
Courtyard by Marriott Fishkill

Courtyard by Marriott Fishkill

3 out of 5
17 Westage Drive Fishkill NY
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $114 total per night from Mar 15 to Mar 16
$114 total
Mar 15 - Mar 16
Total with taxes and fees
8.8/10 Excellent! (753 reviews)
The room was clean and the staff was very helpful .

Reviewed on Mar 2, 2026

Courtyard by Marriott Fishkill
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 $385 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.