Dover Plains Vacations from $380

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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 $792, price is now $380 per person
$380
per person
Feb 9 - Feb 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
7.4/10 Good! (5,413 reviews)
Very nice would stay here again

Reviewed on Dec 9, 2025

Courtyard New York Manhattan/ Midtown East

Courtyard New York Manhattan/ Midtown East

3 out of 5
Manhattan
Price was $1,108, price is now $530 per person
$530
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
9/10 Wonderful! (2,346 reviews)
Room was great, staff was helpful! Disappointed that there was no shuttle to the airport. Also, no free coffee. Had to pay $4 for Starbucks from a machine - not great.

Reviewed on Dec 7, 2025

INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Price was $981, price is now $470 per person
$470
per person
Feb 9 - Feb 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
9.2/10 Wonderful! (2,008 reviews)
Room is great and the staff is excellent 💯

Reviewed on Dec 5, 2025

Harpoon House

Harpoon House

3 out of 5
Price was $976, price is now $518 per person
$518
per person
Feb 12 - Feb 16
found 6 hours ago
Roundtrip flight included
Miami (MIA) to New York (JFK)
8.4/10 Very Good! (147 reviews)
We were looking for a quick overnight in the East End, and the Harpoon House exceeded our expectations in every way. The room was spacious (a suite!) and well-appointed, blending the charm of the original 1648 (!) building with modern amenities and furnishings. We didn't take advantage of the on-property restaurant (formerly Blu Mar), but the menu - by acclaimed chef Rocco DiSpirito - looked excellent, if a bit pricey. Location was ideal, within easy walking distance of all Main Street shops and restaurants, and less than a mile to the beach. And, although things were a bit quieter than in the height of summer - not a bad thing! - we loved being out there for the fall harvest season, with wineries and farms in full swing. All-in-all, our stay at the Harpoon House made for a perfect fall weekend in the Hamptons - highly recommended.

Reviewed on Oct 20, 2025

The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was $877, price is now $468 per person
$468
per person
Feb 27 - Mar 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
9.2/10 Wonderful! (1,002 reviews)
Electric charger readily available on the premises. The staff goes above and beyond to make sure your stay is perfect

Reviewed on Dec 9, 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
$93 nightly
The price is $108 total per night from Dec 16 to Dec 17
$108 total
Dec 16 - Dec 17
Total with taxes and fees
7.6/10 Good! (497 reviews)
Room was clean. Staff was kind. Good complimentary breakfast

Reviewed on Nov 23, 2025

Quality Inn 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
$162 nightly
The price is $186 total per night from Dec 20 to Dec 21
$186 total
Dec 20 - Dec 21
Total with taxes and fees
9/10 Wonderful! (1,000 reviews)
Excellent property, great restaurant, professional prompt management.

Reviewed on Nov 30, 2025

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
$84 nightly
The price is $98 total per night from Dec 20 to Dec 21
$98 total
Dec 20 - Dec 21
Total with taxes and fees
8.8/10 Excellent! (1,005 reviews)
Clean, people very nice, thank you.

Reviewed on Dec 6, 2025

Hampton Inn & Suites Poughkeepsie
See all 870 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 $380 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.