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.
The Fifth Avenue Hotel

The Fifth Avenue Hotel

5 out of 5
Manhattan
Price was CA $2,272, price is now CA $1,338 per person
CA $1,338
per person
Aug 22 - Aug 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.6/10 Exceptional! (244 reviews)
The property was absolutely beautiful- so well decorated! The staff was not only helpful and knowledgeable, but also very kind. If you’re looking for a beautiful luxury property, definitely don’t sleep on this one!

Reviewed on Jul 2, 2026

Radio Hotel

Radio Hotel

4 out of 5
Manhattan
Price was CA $2,820, price is now CA $1,359 per person
CA $1,359
per person
Sep 13 - Sep 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.6/10 Excellent! (2,498 reviews)
Good place in the neighborhood

Reviewed on Jul 13, 2026

The Prince Kitano New York

The Prince Kitano New York

4.5 out of 5
Manhattan
Price was CA $4,246, price is now CA $2,390 per person
CA $2,390
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.4/10 Exceptional! (2,281 reviews)
The only critic is about the breakfast, not f=good at all

Reviewed on Jul 13, 2026

Ink 48 Hotel

Ink 48 Hotel

4.5 out of 5
Manhattan
Price was CA $3,376, price is now CA $1,986 per person
CA $1,986
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.4/10 Very good! (1,710 reviews)
A comfortable and low-key hotel nestled in Hells kitchen with a short distance to some great local dining options, major landmarks, sites (Rockefeller, MOMA, Vessel, The High Line) and just the right distance away from the hectic hustle. Rooms are incredibly spacious, which is a rarity in the city, very comfortable and quiet. All the front desk management and staff were an absolute pleasure and made me feel like I was visiting home away from home.

Reviewed on Jul 13, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $4,792, price is now CA $2,982 per person
CA $2,982
per person
Aug 15 - Aug 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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

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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 $167 per night from Jul 27 to Jul 28
CA $167
CA $194 total
Jul 27 - Jul 28
includes taxes & fees
9/10 Wonderful! (1,022 reviews)
"The room temperature wouldn’t come down to set point. However, Poughkeepsie was dealing with 100 degree temperatures."

Reviewed on Jul 13, 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 $127 per night from Aug 12 to Aug 13
CA $127
CA $146 total
Aug 12 - Aug 13
includes taxes & fees
8.4/10 Very good! (163 reviews)
"Dd"

Reviewed on Jul 10, 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 $130 per night from Jul 19 to Jul 20
CA $130
CA $146 total
Jul 19 - Jul 20
includes taxes & fees
8/10 Very good! (1,013 reviews)
"Great for a lower cost place to stay without sacrificing everything. There is no gym, no pool, no elevator, and poor sound proofing. BUT, guests were respectful during quiet hours, the breakfast was decent, and the staff was helpful and pleasant."

Reviewed on Jul 13, 2026

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 $1,338 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.