Dover Plains Vacation Packages

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

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Top Dover Plains Vacation Deals

Price found within the past 48 hours. Click for updated prices.
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $2,303, price is now CA $1,516 per person
CA $1,516
per person
Dec 8 - Dec 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,004 reviews)

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Save 100% on your flight
Price was CA $3,580, price is now CA $2,201 per person
CA $2,201
per person
Dec 31 - Jan 4
found 15 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to New York (JFK)
9/10 Wonderful! (1,002 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 CA $4,919, price is now CA $3,202 per person
CA $3,202
per person
Dec 2 - Dec 5
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to New York (JFK)
9.2/10 Wonderful! (4,080 reviews)
This hotel is directly on Times Square - great location. Couldn’t have asked for anything more

Reviewed on Oct 28, 2026

Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Manhattan
Save 100% on your flight
Price was CA $2,905, price is now CA $1,897 per person
CA $1,897
per person
Dec 31 - Jan 4
found 15 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)
wonderful stay and well located.....

Reviewed on Oct 28, 2026

JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Save 100% on your flight
Price was CA $4,078, price is now CA $2,724 per person
CA $2,724
per person
Jan 11 - Jan 15
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)
We had an incredible stay at the Essex House last week with our two kids (one is 7 and the other turned 4 on our trip). We booked the king suite, thinking that even though it's NYC and the room will likely be small, it would be the best option for a family of 4. We were SHOCKED at the size of the suite! Not only was it enough room for all of us, it was downright roomy! We had plenty of space for our stay. The amenities and cleanliness of the hotel are superior, room service was delicious (if expensive), and best of all...the guest relations team sent a special surprise gift to our room for our 4 year olds birthday. They sent him balloons, two pieces of cake, and a bag full of stuffies and goodies. He was THRILLED and we were so touched by the thoughtfulness. Both of our kids have already asked if - not only can we go back to New York - but can we stay at the Essex House again! The location was incredible and overall the Essex House played a big part in how wonderful and effortless our trip was. Already looking at dates in the Spring to visit again! Thank you Essex House and your wonderful staff!

Reviewed on Oct 19, 2026

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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 $132 per night from Nov 29 to Nov 30
CA $132
CA $153 total
Nov 29 - Nov 30
includes taxes & fees
Hyatt Place Poughkeepsie / Hudson Valley
Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84

2.5 out of 5
835 Route 52 Fishkill NY
Fully refundable
The price is CA $137 per night from Nov 29 to Nov 30
CA $137
CA $158 total
Nov 29 - Nov 30
includes taxes & fees
Comfort Suites Fishkill near Interstate 84
La Quinta Inn & Suites by Wyndham Danbury

La Quinta Inn & Suites by Wyndham Danbury

3 out of 5
116 Newtown Road Danbury CT
Fully refundableReserve now, pay when you stay
The price is CA $166 per night from Nov 9 to Nov 10
CA $166
CA $191 total
Nov 9 - Nov 10
includes taxes & fees
8.4/10 Very good! (824 reviews)
"Clean room and helpful staff. Good bargain for the price, and I highly recommend this hotel."

Reviewed on Oct 28, 2026

La Quinta Inn & Suites by Wyndham Danbury
See all 877 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 $1,516 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.