Derby Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

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

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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    Plan, book, and manage your trip all in one place

Your Derby Vacation

Reserve a Derby vacation package and get set to experience the best of this lively city. Think about staying in the neighborhood of Downtown New Haven, which is great for shopping, bars and pubs and history. If taking in sights is part of the program during your trip to Derby, check out big attractions like SportsCenter of Connecticut, Eisenhower Park and Ansonia Mall Shopping Center. Check out Expedia's wide range of travel options and book your perfect vacation to Derby today.

Top Derby Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Wall Street Inn

The Wall Street Inn

Manhattan
Save 100% on your flight
CA $1,171
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,005 reviews)
Beautiful hotel, very clean room, great location. By having hotel with validated receipt (saved us $20 overnight), the valet parking garage across the street was quite convenient. However, upon check-in on Saturday 5p, there was an Octoberfest a half-block away and everyone was heavily drinking with lots of DJ music and drunken noise. We asked the front desk about it at check-in but they said it would be quiet by 11:30pm and dismissed our concern. Even with the windows closed on our corner room, the decibel level was too high and lasted till 2:40am! Other guests we spoke to in different parts of the hotel had the same complaint. Hotel should provide earplugs upon arrival, like we received in a Newport, RI hotel in 2022.

Reviewed on Oct 12, 2026

Lotte New York Palace

Lotte New York Palace

Manhattan
Save 100% on your flight
CA $1,425
per person
Dec 20 - Dec 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (2,282 reviews)
location is ideal, large crowds hampered the experience - no taxi, little help w/luggage, long long elevator wait time - note long holiday weekend

Reviewed on Oct 13, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

Save 100% on your flight
CA $2,065
per person
Dec 24 - Dec 27
found 20 hours ago
Roundtrip flight included
Montreal (YUL) to New York (JFK)
9/10 Wonderful! (1,007 reviews)
Great room, nice staff, clean room

Reviewed on Oct 12, 2026

1 Hotel Central Park

1 Hotel Central Park

Manhattan
Save 100% on your flight
CA $3,528
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,007 reviews)
Pendry Natirar

Pendry Natirar

Save 100% on your flight
CA $2,189
per person
Dec 24 - Dec 27
found 20 hours ago
Roundtrip flight included
Montreal (YUL) to New York (JFK)
9.8/10 Exceptional! (21 reviews)

Ready to book your vacation to Derby?

Choose your dates

Derby Hotel Deals

New Haven Hotel

New Haven Hotel

229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
CA $174
CA $200 total
Oct 27 - Oct 28
includes taxes & fees
New Haven Hotel
Trumbull Marriott Shelton

Trumbull Marriott Shelton

180 Hawley Ln Trumbull CT
Fully refundableReserve now, pay when you stay
CA $217
CA $249 total
Oct 25 - Oct 26
includes taxes & fees
Trumbull Marriott Shelton
The Circle Hotel Fairfield

The Circle Hotel Fairfield

417 Post Road Fairfield CT
CA $241
CA $291 total
Nov 9 - Nov 10
includes taxes & fees
8.8/10 Excellent! (1,481 reviews)
"We didn't use much of the amenities so I cannot speak to that but the bed was the comfiest bed we've ever experienced. The front desk were friendly and the room was clean. The remote check-in/check-out was super convenient, too. We will absolutely stay again when visiting family."

Reviewed on Oct 12, 2026

The Circle Hotel Fairfield
See all 1,189 properties in Derby
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 Derby attractions

Osborndale State Park

You can take time to visit Osborndale State Park during your travels to Derby. Stroll along the beaches or experience the live music in this family-friendly area.
See properties

Osborne Homestead Museum

You can spend time exploring the galleries in Osborne Homestead Museum during your trip to Derby. Amble around this family-friendly area's beaches or experience its live music.
See properties

Frequently asked questions

How much does a Derby vacation package cost?
Offering great value package deals from CA $1,171 on Expedia, you'll be thrilled with how little a vacation to Derby costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Derby?
To pick up cheap Derby vacation packages, plan your getaway outside of peak times such as school holidays. You'll generally find lower prices and better availability when it's less busy.
How many days is enough for Derby?
The ideal duration of your Derby vacation depends on what you'd like to see. Typically, a few days to a week will give you plenty of time to tick off all the leading sights and explore some hidden treasures along the way.
How to find the best Derby package deals?
Use Expedia's handy filters to help you find some tempting Derby package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or search for Derby package deals in the low season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Derby vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking flights and stays individually. Better still, you can customize your Derby trip to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Derby?
If you're planning an impromptu Derby trip, browse our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can find sensational deals on your hotels and flights by booking well in advance.
How to plan a trip to Derby?
  1. Choose the right time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to go to Derby.
  2. Set your budget: Consider costs like transportation, flights and meals when working out how much to save for your trip to Derby. Then, choose a property that matches your budget, whether that's a low-cost stay or a deluxe retreat.
  3. Work out your trip length: Think about how long you'd like to spend discovering Derby. Plan your days so you can get to all the attractions and activities you're interested in without rushing.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left now is to pick a Derby vacation package that brings all your bookings together.

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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.