Dover Plains Vacation Packages

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    Save up to CA $1,096 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 Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was CA $882, price is now CA $560 per person
CA $560
per person
Oct 7 - Oct 9
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)
This place is the bomb. Loved our suite, loved the pool and the breakfast was wonderful

Reviewed on Aug. 12, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $6,783, price is now CA $3,371 per person
CA $3,371
per person
Nov 9 - Nov 16
found 1 day ago
Roundtrip flight included
Montreal (YUL) to New York (JFK)
8.8/10 Excellent! (1,009 reviews)
Wonderful room and staff. The Brooklyn Bridge view was amazing.

Reviewed on Aug. 21, 2025

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
Price was CA $5,106, price is now CA $3,061 per person
CA $3,061
per person
Nov 9 - Nov 16
found 1 day ago
Roundtrip flight included
Montreal (YUL) to New Haven (HVN)
No reviews
New York Marriott Marquis

New York Marriott Marquis

4.5 out of 5
Manhattan
Price was CA $1,619, price is now CA $1,001 per person
CA $1,001
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (3,915 reviews)
The only problem I had with this hotel was that at check-in, a black woman, a bit rude because I didn't want to pay for the upgrade she was offering, assigned me a room (1460) with a view that was worse than terrible. I immediately went down to the front desk to complain, and a very kind gentleman assisted me. He understood the situation and moved me to an excellent room (3509) with a partial view of Times Square.

Reviewed on Aug. 20, 2025

Omni Berkshire Place

Omni Berkshire Place

4 out of 5
Manhattan
Price was CA $2,164, price is now CA $1,415 per person
CA $1,415
per person
Oct 21 - Oct 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (1,951 reviews)
We had a comfy stay!

Reviewed on Aug. 18, 2025

Ready to book your vacation to Dover Plains?

 

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Dover Plains Hotel Deals

Quality Inn Poughkeepsie

Quality Inn Poughkeepsie

2.5 out of 5
536 Haight Ave, Building A, Poughkeepsie, NY
Fully refundableReserve now, pay when you stay
The price is CA $143 per night from Sep 8 to Sep 9
CA $143
CA $166 total
Sep 8 - Sep 9
includes taxes & fees
7.6/10 Good! (394 reviews)
"The outside building is terrible and in complete disrepair. The actual “inside” building is much better but at the moment it has a mouse problem."

Reviewed on Aug. 17, 2025

Quality Inn Poughkeepsie
Hotel Zero Degrees Danbury

Hotel Zero Degrees Danbury

4 out of 5
15 Milestone Road, Danbury, CT
Fully refundableReserve now, pay when you stay
The price is CA $212 per night from Aug 31 to Sep 1
CA $212
CA $244 total
Aug 31 - Sep 1
includes taxes & fees
9/10 Wonderful! (1,005 reviews)
"Excellent property with great restaurant"

Reviewed on Aug. 18, 2025

Hotel Zero Degrees Danbury
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 $129 per night from Aug 24 to Aug 25
CA $129
CA $148 total
Aug 24 - Aug 25
includes taxes & fees
8.2/10 Very Good! (1,003 reviews)
"Very outdated"

Reviewed on Aug. 19, 2025

La Quinta Inn & Suites by Wyndham Danbury
See all 866 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
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Family Vacations
Family Vacations

Frequently asked questions

How much does a Dover Plains vacation package cost?
You'll find cheap prices from CA $560 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.