Dover Plains Vacations from $543

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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 $1,017, price is now $543 per person
$543
per person
May 7 - May 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
8.8/10 Excellent! (7,026 reviews)
Pros: Staff was friendly. Bed was comfortable. Room was clean. The location is fantastic for exploring the city! Cons: zero amenities-no fridge/microwave/coffee maker/vending machines. Bathroom is terrible with only a small pedestal sink and an old tub and it’s very small. Toilet didn’t flush well at all. The TV is old and kept shutting off. Overall it suited the need and provided a comfortable bed after long days walking in the city. Despite the lack of amenities we would likely stay there again for the convenience of its location!

Reviewed on Mar 18, 2026

OYO Times Square

OYO Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was $1,340, price is now $765 per person
$765
per person
May 20 - May 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
7/10 Good! (1,782 reviews)
1. Beds squeak so bad - if you breathe the bed squeaks. 2. 5am - the trash truck or whomever start honking their horns ~ ALL MORNING LONG. There is no reprieve from this. 3. No WiFi 4. No laundry/washer available 5. We were never really sure when our room was going to be serviced. 75% it was, but yea… 6. Thin bathtowels 7 The TV has this weird subtitle thing that describes everything happening on the show your watching; there is no shutting this off. Not even worth watching. 8. The shower water is SO HOT it will burn ur skin. Please leave it on minimum for a barely acceptable shower. 9. Mattresses are very… broken in. 10. The convenience of the location was great but for the price, I probably could have went somewhere better. Lesson learned.

Reviewed on Mar 18, 2026

Topping Rose House

Topping Rose House

4.5 out of 5
Save 100% on your flight
Price was $1,381, price is now $802 per person
$802
per person
May 6 - May 9
found 4 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
9.2/10 Wonderful! (143 reviews)
Everything and everyone was just lovely! Comfortable Welcoming Great restaurant

Reviewed on Feb 22, 2026

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Save 100% on your flight
Price was $1,941, price is now $1,232 per person
$1,232
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $1,328, price is now $849 per person
$849
per person
May 7 - May 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,450 reviews)
Chris is the heart and soul of this hotel. He anticipates what you need before you even ask! He is fun, kind, and very professional!

Reviewed on Mar 18, 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
$179 nightly
The price is $206 total per night from Mar 22 to Mar 23
$206 total
Mar 22 - Mar 23
Total with taxes and fees
9.2/10 Wonderful! (1,002 reviews)
Comfortable and clean - we will be back

Reviewed on Mar 15, 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
$102 nightly
The price is $118 total per night from Apr 5 to Apr 6
$118 total
Apr 5 - Apr 6
Total with taxes and fees
9/10 Wonderful! (1,001 reviews)
It was a nice stay, no complaints. We will definitely stay here again next time we are in the area!

Reviewed on Mar 17, 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 22 to Mar 23
$114 total
Mar 22 - Mar 23
Total with taxes and fees
8.8/10 Excellent! (756 reviews)
Staff was very nice . Gave us water bottles , and i loved that they didn’t come knocking on the door as soon as it was checkout time

Reviewed on Mar 18, 2026

Courtyard by Marriott Fishkill
See all 854 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 $543 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.