Dover Plains Vacations from $379

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The Latest Dover Plains vacation packages

Price found within the past 48 hours. Click for updated prices.
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Save 100% on your flight
per person
Nov 4 - Nov 7
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)
This place is the bomb. Loved our suite, loved the pool and the breakfast was wonderful

Reviewed on Aug 12, 2025

Sound View Greenport

Sound View Greenport

4 out of 5
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.4/10 Very Good! (548 reviews)
Thank you Adrian. She was wonderful and made my mother’s birthday special. Every interaction we had with the staff was positive. The halyard served a delicious lobster roll in a beautiful setting. We will be back.

Reviewed on Aug 9, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
per person
Sep 21 - Sep 23
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,008 reviews)
Loved everything about it

Reviewed on Aug 6, 2025

The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
Save 100% on your flight
per person
Oct 12 - Oct 17
found 16 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
8.8/10 Excellent! (495 reviews)
Great hotel. Staff were amazing! Loved that you could use their sister property by the beach and stay in town. Just did not like having to pay for overnight parking.

Reviewed on Aug 14, 2025

Hotel St. James

Hotel St. James

2.5 out of 5
Manhattan
Save 100% on your flight
per person
Oct 18 - Oct 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (6,194 reviews)
Right off of Times Square, so walkable to all the theaters and great restaurants. Very very clean. The staff is fun and informative.

Reviewed on Aug 17, 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
$103 nightly
The price is $120 total per night from Sep 8 to Sep 9
$120 total
Sep 8 - Sep 9
Total includes taxes and fees
7.6/10 Good! (389 reviews)
"Room was clean and neat. Breakfast had limited options but was good enough. Staff was very friendly and professional. Will stay again should my business bring me back this way."

Reviewed on Aug 11, 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
$170 nightly
The price is $196 total per night from Aug 31 to Sep 1
$196 total
Aug 31 - Sep 1
Total includes taxes and fees
9/10 Wonderful! (1,003 reviews)
"Nice hotel, could use a vanity mirror in the bathroom. Quiet, clean, modern and overall I would recommend it."

Reviewed on Aug 13, 2025

Hotel Zero Degrees Danbury
Holiday Inn Express Poughkeepsie by IHG

Holiday Inn Express Poughkeepsie by IHG

2.5 out of 5
2750 South Road, Poughkeepsie, NY
Fully refundable
$109 nightly
The price is $127 total per night from Aug 24 to Aug 25
$127 total
Aug 24 - Aug 25
Total includes taxes and fees
8.6/10 Excellent! (1,006 reviews)
"The hotel, service, and room were fine; the bed was comfortable, and the breakfast had a fair variety of food options. However, finding a stained sofa was gross; we couldn't sit on it. The bathroom needs a deep cleaning. It doesn't seem that the pool will be repaired anytime soon, which shows that ..."

Reviewed on Aug 17, 2025

Holiday Inn Express Poughkeepsie by IHG
See all 873 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.

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Frequently asked questions

How much does a Dover Plains vacation package cost?
You'll find cheap prices from $379 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.