Town of Dover Vacation Packages

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Your Town of Dover Vacation

Our vacation packages to Town of Dover make it a cinch to experience this exciting destination. From its history to all its other enticing highlights, you'll never be short of reasons to go. Can't decide where to stay first? Dover Plains is among the most popular cities to explore during a trip to Town of Dover. Start packing your suitcase, because your Town of Dover vacation is just clicks away with Expedia.

Top Town of Dover Vacation Deals

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

Night Hotel Broadway

3 out of 5
Manhattan
Price was CA $1,617, price is now CA $1,017 per person
CA $1,017
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to New York (JFK)
7.6/10 Good! (3,805 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 8 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to New York (JFK)
9/10 Wonderful! (1,002 reviews)
Great location; great service. Seemed to be a problem with the room heat/AC, but the weather was mild in NYC that week, so I cannot fully confirm.

Reviewed on Oct 26, 2026

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
Save 100% on your flight
Price was CA $6,819, price is now CA $4,245 per person
CA $4,245
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to New York (JFK)
9.2/10 Wonderful! (713 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)
Everton is good

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 8 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

Town of Dover Hotel Deals

Ethan Allen Hotel

Ethan Allen Hotel

3.5 out of 5
21 Lake Avenue Extension Danbury CT
Fully refundableReserve now, pay when you stay
The price is CA $147 per night from Nov 15 to Nov 16
CA $147
CA $169 total
Nov 15 - Nov 16
includes taxes & fees
Ethan Allen Hotel
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 $148 per night from Nov 10 to Nov 11
CA $148
CA $171 total
Nov 10 - Nov 11
includes taxes & fees
Hyatt Place Poughkeepsie / Hudson Valley
Heritage Hotel, Golf & Conference Center

Heritage Hotel, Golf & Conference Center

3.5 out of 5
522 Heritage Road Southbury CT
The price is CA $151 per night from Nov 19 to Nov 20
CA $151
CA $198 total
Nov 19 - Nov 20
includes taxes & fees
Heritage Hotel, Golf & Conference Center
See all 919 properties in Town of Dover
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

Frequently asked questions

How much does a Town of Dover vacation package cost?
Tailor make your Town of Dover vacation package from a low CA $1,017. Pick from any combination of flights, hotels and rental cars to build the trip you've been dreaming about. Be sure to add on one or two experiences!
How do I get a cheap travel package to Town of Dover?
Creating your own Town of Dover vacation package with Expedia is an easy way to save. We have over 550 air carriers and 1,000,000 hotels across the globe. With such a wonderful range to pick from, you'll have no difficulty putting together your perfect escape.
What are the top hotels in Town of Dover?
When it comes to properties in Dover Plains, Campers Paradise, Cozy Tents, Hot Showers and Glamping, Family Fun, Pet Friendly are two terrific options. If you're also spending time in Wingdale, Welcome To The Lake: Your 4 - Season Private Paradise Awaits and Cabin - 3 Bedroom Property are waiting to welcome you.
How far in advance should I book my Town of Dover vacation?
Your best bet is to book early. Airlines generally release flights nearly 12 months prior to departure, and this is an excellent opportunity to score some rock-bottom prices. Just been told you need to take all your vacation days next month? No sweat. Expedia are never short of fantastic bargains to send you off on the getaway of your dreams, at a price you can afford.
What does an Expedia Town of Dover travel package include?
With Expedia, you can select a combination of car rentals, hotels and flights to build your ideal Town of Dover travel package. Once you've made your booking, you can add on fun stuff like tours and experiences. Remember, the more you bundle, the bigger the savings!
What should I know before booking a Town of Dover travel package?
You can save big by combining your hotels, flights and rental cars. Once you've created your package, you can add on things like activities or sightseeing tours. Your next awesome vacation is only a few clicks away.
Can I choose my airline with a Town of Dover Expedia vacation package?
With a vacation package, you're in control. Whether you're looking to fly to Town of Dover in coach or first class, simply choose from the available airline options. Expedia has access to over 550 airline partners worldwide.
If I'm not able to travel, can I cancel my Town of Dover vacation package?
We totally understand that the universe can throw the odd curveball. If you've locked in a Town of Dover vacation package and have to change or cancel it, we can help. We suggest having a look at our Customer Service Portal first for information. But generally speaking, if you've taken out your package in the last 24 hours, you may be able to cancel or amend your itinerary at no cost. If it's been more than 24 hours, your hotel, airline or car rental company may impose a charge.

Stay near popular Town of Dover attractions

Pawling Nature Reserve

You can take time to visit Pawling Nature Reserve during your travels to Wingdale.
See properties
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.