Chelsea Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Chelsea Vacation
The best way to experience this lively city is with a custom-made Chelsea vacation package. Stay in the neighborhood of Poughkeepsie Waterfront, which is great for families, history and culture or go someplace else — our packages are all about you. Every trip to Chelsea needs a well-designed itinerary. Fill yours with major attractions like Poughkeepsie Galleria, Bowdoin Park and Dutchess Stadium. Don't delay visiting this destination any longer. Your dream Chelsea vacation is a couple of clicks away with Expedia.
Top Chelsea Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Manhattan Times Square
Manhattan
CA $1,477
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (3,936 reviews)
The location is very good and the breakfast is excellent; my only complaint is that the TV doesn't work properly—you have to connect it to your phone, but it keeps disconnecting, forcing you to start all over again.
Reviewed on Sep 3, 2026
Hotel Riu Plaza New York Times Square
Manhattan
CA $1,496
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (3,334 reviews)
We were here during the World Cup. We had a great chic and clean room. We loved the action around the hotel.
Reviewed on Sep 3, 2026
Ready to book your vacation to Chelsea?
Chelsea Hotel Deals
Overlook Lodge at Bear Mountain
55 Hessian Drive Bear Mountain NY
Fully refundableReserve now, pay when you stay
CA $139
CA $171 total
Sep 7 - Sep 8
includes taxes & fees
Holiday Inn Express Poughkeepsie by IHG
2750 South Road Poughkeepsie NY
Fully refundable
CA $132
CA $153 total
Oct 4 - Oct 5
includes taxes & fees
Hyatt Place Poughkeepsie / Hudson Valley
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
CA $138
CA $160 total
Sep 24 - Sep 25
includes taxes & fees
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.
Frequently asked questions
How much does a Chelsea vacation package cost?
You can snap up a vacation package to this top destination from CA $1,477 on Expedia. However, how much your vacation to Chelsea costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Chelsea?
You're likely to find reduced prices and better availability in January, February and March. Check out our cheap Chelsea vacation packages and you could score some great off-season discounts.
How many days is enough for Chelsea?
The ideal length of your Chelsea vacation depends on what you'd like to do and see. Generally, a handful of days to a week will give you time to go to all the top attractions and explore some hidden spots along the way.
How to find the best Chelsea package deals?
Finding a cheap Chelsea package deal is a cinch with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your maximum budget, apply a couple of filters and see what's available. You can fine-tune your search by "Amenities," "Property type," "Traveller experience" and more. Sort the results by "Price: low to high" to view the most economical Chelsea package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Chelsea vacation as a package?
You can enjoy significant savings on your next Chelsea break by booking a tailored vacation package. Click on the "Package" heading, then enter your destination and travel dates to view the best airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Chelsea?
If you have your Chelsea vacation dates finalized, book as early as you can to grab some outstanding deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spur-of-the-moment trips? Our last-minute deals are ideal for impromptu escapes.
How to plan a trip to Chelsea?
- Choose when to get away: Check your calendar and get your bags packed. Your preferred season and the activities available will also help you decide when to escape to Chelsea.
- Work out your budget: Make sure you have enough money to cover everything from food and transportation to flights and experiences. Your accommodations will probably be the biggest expense during your trip to Chelsea.
- Decide your trip length: Think about how long you'd like to spend exploring Chelsea. Plan your itinerary so you can get to all the activities and attractions you're interested in at a leisurely pace.
- Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a personalized Chelsea vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
