Dover Plains Vacations from $450

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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
Price was $852, price is now $450 per person
$450
per person
May 7 - May 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
8.8/10 Excellent! (7,024 reviews)
Only complaint is the water didnt get warm to take a shower.

Reviewed on Mar 6, 2026

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Price was $1,755, price is now $917 per person
$917
per person
May 28 - Jun 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
9.8/10 Exceptional! (1,411 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

Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Manhattan
Price was $1,871, price is now $1,034 per person
$1,034
per person
May 28 - Jun 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,001 reviews)
Excellent stay, very clean spacious rooms. Location is great - close to everything. Only downfall was the bathroom, very tiny with a pedestal sink right next to the toilet, not great for women who need to get ready.

Reviewed on Feb 24, 2026

OYO Times Square

OYO Times Square

4 out of 5
Manhattan
Price was $1,228, price is now $686 per person
$686
per person
May 14 - May 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
7/10 Good! (1,773 reviews)
Great experience Personal was amazing and very helpful I will recommend 100%

Reviewed on Feb 26, 2026

Margaritaville Resort Times Square

Margaritaville Resort Times Square

4 out of 5
Manhattan
Price was $1,611, price is now $909 per person
$909
per person
May 14 - May 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,941 reviews)
Excellent place to stay

Reviewed on Mar 6, 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 29 to Mar 30
$178 total
Mar 29 - Mar 30
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
$94 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! (1,009 reviews)
The staff was amazing, the room was clean, but the walls were very thin.

Reviewed on Mar 5, 2026

Hampton Inn & Suites Poughkeepsie
See all 843 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 $450 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.