Dover Plains Vacations from $296

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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
Price was $574, price is now $296 per person
$296
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)
Amazing stay. Great food, great bed, great staff

Reviewed on Nov 5, 2025

Fouquet's New York

Fouquet's New York

5 out of 5
Manhattan
Price was $1,556, price is now $817 per person
$817
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
9.8/10 Exceptional! (58 reviews)
Lovely staff. Incredible property. The hype is real. This is by far and away the nicest property we’ve stayed at in Manhattan in a long time.

Reviewed on Oct 10, 2025

INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Save 100% on your flight
Price was $702, price is now $374 per person
$374
per person
Jan 8 - Jan 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (2,030 reviews)
No balcony. Nosey. Mattress uncomfortable

Reviewed on Nov 6, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $1,629, price is now $868 per person
$868
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,012 reviews)
Nice hotel , needs a bit of tender love and care !

Reviewed on Oct 14, 2025

The Mansion at Glen Cove

The Mansion at Glen Cove

4 out of 5
Save 100% on your flight
Price was $599, price is now $327 per person
$327
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (NYC)
7/10 Good! (1,001 reviews)
perfect stay. love the nature and the vibe there. will be best for vacation.

Reviewed on Nov 2, 2025

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Dover Plains Hotel Deals

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
$99 nightly
The price is $115 total per night from Dec 5 to Dec 6
$115 total
Dec 5 - Dec 6
Total with taxes and fees
8.6/10 Excellent! (1,012 reviews)
Service and staff was A+++++

Reviewed on Nov 2, 2025

Hampton Inn & Suites 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 Nov 9 to Nov 10
$186 total
Nov 9 - Nov 10
Total with taxes and fees
9/10 Wonderful! (1,003 reviews)
The ambiance was nice and everything smelled VERY clean

Reviewed on Nov 5, 2025

Hotel Zero Degrees Danbury
Quality Inn & Suites Fishkill South near I-84

Quality Inn & Suites Fishkill South near I-84

2.5 out of 5
849 Route 52, Fishkill, NY
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $122 total per night from Dec 7 to Dec 8
$122 total
Dec 7 - Dec 8
Total with taxes and fees
8.8/10 Excellent! (1,006 reviews)
Nice stay. Easy check-in.

Reviewed on Oct 26, 2025

Quality Inn & Suites Fishkill South near I-84
See all 860 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 $296 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.