Dover Plains Holidays

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    Save up to S$1,300 when you book a flight and hotel together*

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Dover Plains Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Ridge Hotel

The Ridge Hotel

3 out of 5
Manhattan
Save 100% on your flight
Price was S$1,754, price is now S$1,133 per person
S$1,133
per person
4 Sept - 9 Sept
found 1 day ago
Return flight included
Toronto (YTO) to New York (JFK)
8.2/10 Very good! (1,156 reviews)
This is an excellent choice if looking to stay in the Lower east side. Extremely close to public transit, lots of shopping, entertainment, and restaurants. The area skews a bit young because it's a few blocks from NYU, but it's an incredible value if you're just looking for a home base to store your suitcase and sleep at night while exploring the city during the day.

Reviewed on 18 Jul, 2026

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Save 100% on your flight
Price was S$2,627, price is now S$1,495 per person
S$1,495
per person
4 Sept - 9 Sept
found 1 day ago
Return flight included
Toronto (YTO) to New York (JFK)
9.6/10 Exceptional! (1,617 reviews)
This hotel is adorable. Great location. Rooms are a great size. We will be back!

Reviewed on 17 Jul, 2026

Marco LaGuardia Hotel

Marco LaGuardia Hotel

3.5 out of 5
Queens
Save 100% on your flight
Price was S$2,472, price is now S$1,517 per person
S$1,517
per person
4 Sept - 9 Sept
found 1 day ago
Return flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (1,117 reviews)

42 Hotel

42 Hotel

3.5 out of 5
Save 100% on your flight
Price was S$1,969, price is now S$1,289 per person
S$1,289
per person
4 Sept - 9 Sept
found 1 day ago
Return flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (918 reviews)

Sela V Hotel

Sela V Hotel

4 out of 5
Save 100% on your flight
Price was S$1,739, price is now S$1,144 per person
S$1,144
per person
4 Sept - 9 Sept
found 1 day ago
Return flight included
Toronto (YTO) to New York (JFK)
9.6/10 Exceptional! (9 reviews)

Top hotels in Dover Plains

Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

3 out of 5
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
The price is S$165 per night from 10 Aug to 11 Aug
S$165
10 Aug - 11 Aug
includes taxes & fees
Hyatt Place Poughkeepsie / Hudson Valley
Spark by Hilton Fishkill

Spark by Hilton Fishkill

3 out of 5
20 Schuyler Blvd Fishkill NY
Fully refundableReserve now, pay when you stay
The price is S$134 per night from 2 Aug to 3 Aug
S$134
2 Aug - 3 Aug
includes taxes & fees
Spark by Hilton Fishkill
DoubleTree by Hilton Poughkeepsie Convention Center

DoubleTree by Hilton Poughkeepsie Convention Center

4 out of 5
40 Civic Center Plz Poughkeepsie NY
Fully refundableReserve now, pay when you stay
The price is S$177 per night from 30 Jul to 31 Jul
S$177
30 Jul - 31 Jul
includes taxes & fees
DoubleTree by Hilton Poughkeepsie Convention Center
See all 863 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.

Stay near popular Dover Plains attractions

Dover Plains Stone Church

A natural cavern with a 30-foot waterfall cascading through its gothic cathedral-like entrance. Hike the serene tree-lined path along Stone Church Brook to experience this geological wonder up close.
See properties

Frequently asked questions

How much does a Dover Plains holiday package cost?
You'll find cheap prices from S$1,133 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 holiday to Dover Plains costs.
What are the cheapest months to go to Dover Plains?
Travel in the off-season and you're likely to score cheap Dover Plains holiday packages. Remember that public holidays and major local events can have an impact on prices, so do your research before you go.
How many days is enough for Dover Plains?
Usually, a handful of days is enough to go to the top attractions during your Dover Plains holiday. But if you'd like to have some time to rest or take day trips, think about extending your trip.
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 holiday as a package?
Expedia holiday 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 personalised Dover Plains holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday 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.
How to plan a trip to Dover Plains?

  1. Choose the right time to travel: Your schedule, favourite season and the type of weather you enjoy can all impact your decision on when to travel to Dover Plains.
  2. Work out your budget: Ensure you have enough money to pay for everything from transportation and meals to airfares and activities. Your accommodation will probably be the largest expense during your trip to Dover Plains.
  3. Decide your trip length: Think about how long you want to spend exploring Dover Plains. Plan your days so you can get to all the attractions and activities you're interested in without rushing.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a customised Dover Plains holiday package.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.