Dover Plains Vacation Packages

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Top Dover Plains Vacation Deals

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

Ink 48 Hotel

4.5 out of 5
Manhattan
Price was CA $1,703, price is now CA $1,160 per person
CA $1,160
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip flight included
Montreal (YUL) to New York (JFK)
8.4/10 Very good! (1,710 reviews)
Staff was very helpful and the room was very clean.

Reviewed on Jul 14, 2026

Topping Rose House

Topping Rose House

4.5 out of 5
Price was CA $14,994, price is now CA $9,524 per person
CA $9,524
per person
Aug 16 - Aug 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (152 reviews)
Amazing

Reviewed on May 29, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $4,199, price is now CA $2,720 per person
CA $2,720
per person
Sep 17 - Sep 20
found 1 hour ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,006 reviews)
Love all the plants that were included in the decor. Top notch quality.

Reviewed on Jul 14, 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was CA $2,816, price is now CA $1,906 per person
CA $1,906
per person
Sep 9 - Sep 13
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to New York (JFK)
9/10 Wonderful! (3,130 reviews)
The staff had great attitudes and were welcoming and informative.

Reviewed on Jul 16, 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was CA $2,659, price is now CA $1,812 per person
CA $1,812
per person
Sep 9 - Sep 13
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to New York (JFK)
9.2/10 Wonderful! (3,652 reviews)
This is my third stay at this hotel. And while here, I scheduled another visit at Christmas time because New York is beautiful in holiday season. Every Hotel employee you come in contact with is so helpful and kind. The rooms are spotless. They are comfortable. Breakfast buffet is fantastic but honestly is on the pricey side. Of course it’s within close walking distance to many restaurants, but there is also a little café, grab and go restaurant right in the lobby of the hotel. I’ve purchased a number of different foods, snacks, and they’ve been excellent. You can’t go wrong choosing this hotel for your stay.

Reviewed on Jul 16, 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 $162 per night from Aug 9 to Aug 10
CA $162
CA $188 total
Aug 9 - Aug 10
includes taxes & fees
9/10 Wonderful! (1,029 reviews)
"The staff at the front desk, Michael and Sara were very polite, helpful and professional. The cleaning staff was helpful and so was the breakfast staff. The bed was super comfortable and the rooms were clean. The only thing I wish our room had was a microwave…besides that everything was great. I’ll ..."

Reviewed on Jul 16, 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 $133 per night from Aug 6 to Aug 7
CA $133
CA $153 total
Aug 6 - Aug 7
includes taxes & fees
8.4/10 Very good! (166 reviews)
"Clean and quiet. Comfortable room and bed"

Reviewed on Jul 14, 2026

Spark by Hilton Fishkill
SureStay Plus Hotel by Best Western Highland Poughkeepsie

SureStay Plus Hotel by Best Western Highland Poughkeepsie

2.5 out of 5
3423 US Highway 9W Highland NY
Fully refundableReserve now, pay when you stay
The price is CA $125 per night from Aug 16 to Aug 17
CA $125
CA $140 total
Aug 16 - Aug 17
includes taxes & fees
SureStay Plus Hotel by Best Western Highland Poughkeepsie
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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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 $1,160 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.

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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.