Dover Plains Vacations from $255

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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 $543, price is now $255 per person
$255
per person
Feb 19 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
7.4/10 Good! (5,413 reviews)
Great area and great selection

Reviewed on Jan 14, 2026

Hotel Alameda Highline

Hotel Alameda Highline

4.5 out of 5
Manhattan
Price was $3,676, price is now $741 per person
$741
per person
Mar 11 - Mar 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
7.6/10 Good! (793 reviews)
No frills but good location and meets all the needs.

Reviewed on Jan 4, 2026

INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Price was $718, price is now $352 per person
$352
per person
Feb 19 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (2,008 reviews)
excellent location and large room and bathroom

Reviewed on Jan 14, 2026

The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was $892, price is now $469 per person
$469
per person
Mar 26 - Mar 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)
The only issues was the lack of insulation. You can hear people talking throughout the halls from the room

Reviewed on Jan 10, 2026

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Save 100% on your flight
Price was $2,094, price is now $1,141 per person
$1,141
per person
Mar 9 - Mar 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New Haven (HVN)
No reviews
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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
$155 nightly
The price is $179 total per night from Jan 18 to Jan 19
$179 total
Jan 18 - Jan 19
Total with taxes and fees
9/10 Wonderful! (1,003 reviews)
,

Reviewed on Jan 8, 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
$89 nightly
The price is $101 total per night from Feb 1 to Feb 2
$101 total
Feb 1 - Feb 2
Total with taxes and fees
8.8/10 Excellent! (1,009 reviews)
The room was clean and the staff was nice, the location was a bit in the middle of nowhere but I liked the quiet and there was plenty of food options around! Overall a great place to stay

Reviewed on Jan 13, 2026

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 Jan 23 to Jan 24
$109 total
Jan 23 - Jan 24
Total with taxes and fees
8.8/10 Excellent! (1,000 reviews)
Team is friendly, professional and helpful. Room was clean and comfy. Breakkfast is well maintained with a variety of options. Love the make your own waffles and the potatoes andyogurt selections.

Reviewed on Jan 12, 2026

Hampton Inn & Suites Poughkeepsie
See all 853 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 $255 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.