Dover Plains Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Dover Plains Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
Price was CA $3,038, price is now CA $1,807 per person
CA $1,807
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to New York (JFK)
9.2/10 Wonderful! (685 reviews)
Great location, great view

Reviewed on Jul 5, 2026

Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Manhattan
Price was CA $3,721, price is now CA $1,910 per person
CA $1,910
per person
Sep 18 - Sep 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
7.4/10 Good! (3,239 reviews)
Very convenient location and very attentive staff. Thanks for another great stay!

Reviewed on Jul 10, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $4,087, price is now CA $2,411 per person
CA $2,411
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to New York (JFK)
9/10 Wonderful! (1,006 reviews)
Fabulous experience. Front desk staff was extremely helpful, friendly, and efficient. Especially while checking-in. Would come back again! Rooms are thoughtfully designed and have amazing views!

Reviewed on Jul 5, 2026

The St. Regis New York

The St. Regis New York

5 out of 5
Manhattan
Price was CA $3,827, price is now CA $2,309 per person
CA $2,309
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to New York (JFK)
9.2/10 Wonderful! (284 reviews)
little far from time square.

Reviewed on Jun 30, 2026

Mandarin Oriental, New York

Mandarin Oriental, New York

5 out of 5
Manhattan
Price was CA $3,296, price is now CA $2,016 per person
CA $2,016
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to New York (JFK)
9.2/10 Wonderful! (651 reviews)
Amazing hotel, staff make the whole experience, bar is great. Reception and concierge team are excellent, in particular Lauren who made check in a breeze. Gym and pool are excellent for a New York hotel.

Reviewed on Jun 21, 2026

Ready to book your vacation to Dover Plains?

 

Choose your dates

Dover Plains Hotel Deals

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 CA $167 per night from Aug 10 to Aug 11
CA $167
CA $194 total
Aug 10 - Aug 11
includes taxes & fees
9/10 Wonderful! (1,015 reviews)
"The staff was very friendly. The rooms were very clean and the breakfast was awesome overall, a very pleasant stay"

Reviewed on Jul 9, 2026

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 CA $128 per night from Jul 30 to Jul 31
CA $128
CA $148 total
Jul 30 - Jul 31
includes taxes & fees
8.4/10 Very good! (163 reviews)
"Dd"

Reviewed on Jul 10, 2026

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 CA $162 per night from Jul 23 to Jul 24
CA $162
CA $190 total
Jul 23 - Jul 24
includes taxes & fees
8.4/10 Very good! (1,015 reviews)
"I was caught in a major storm and unable to physically get to the hotel and they would not refund the charge."

Reviewed on Jul 10, 2026

DoubleTree by Hilton Poughkeepsie Convention Center
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Stay near popular Dover Plains attractions

Dover Plains Stone Church

Commune with nature and explore the great outdoors at Dover Plains Stone Church during your travels in Dover Plains.
See properties

Frequently asked questions

How much does a Dover Plains vacation package cost?
You'll find cheap prices from CA $1,807 on Expedia for your Dover Plains escape. However, a range of factors like your choice of hotel, the season and length of stay will influence how much your vacation to Dover Plains costs.
What are the cheapest months to go to Dover Plains?
To score cheap Dover Plains vacation packages, plan your getaway outside of peak periods like public holidays and major festivals. You'll generally find better availability and lower prices when it's less busy.
How many days is enough for Dover Plains?
Typically, a handful of days is enough to see the main attractions during your Dover Plains vacation. However, if you prefer to have some time to relax or take day trips, think about extending your itinerary.
How to find the best Dover Plains package deals?
Use Expedia's handy filters to help you find some tempting Dover Plains package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your break for midweek, or search for Dover Plains package deals in the off-peak season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package well in advance.
Is it cheaper to book a Dover Plains vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll generally get a better deal than booking each component individually. And you'll still have the freedom to create a customized Dover Plains vacation by choosing your favourite airline, accommodation type and car class.
When to book a vacation package to Dover Plains?
Score amazing discounts by booking your flights in advance with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for an impromptu Dover Plains adventure.
How to plan a trip to Dover Plains?

  1. Choose when to go: Check your diary and pack your bags. Your preferred season and the activities on offer will also help you decide when to escape to Dover Plains.
  2. Set your budget: Factor in costs such as flights, food and transportation when working out how much to save for your trip to Dover Plains. Then, select a hotel that suits your budget, whether that's an affordable stay or a lavish retreat.
  3. Decide how long to go away for: Now that you're more familiar with Dover Plains, you can work out the right length of your break. Put together a rough itinerary and give yourself enough time to cover everything you want to see.
  4. Combine your accommodations and airfare: After you've settled on your trip dates and duration, book the right Dover Plains vacation package for you.

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.