Chelsea Vacation Packages

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

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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.
Radio Hotel

Radio Hotel

4 out of 5
Manhattan
Price was CA $1,394, price is now CA $942 per person
CA $942
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
8.6/10 Excellent! (2,498 reviews)
There are escorts and crackhds in this hotel. Read about the neighborhood it’s in. Washington Heights is terrible.

Reviewed on Jul 20, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $4,207, price is now CA $2,657 per person
CA $2,657
per person
Sep 2 - Sep 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,006 reviews)

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was CA $2,621, price is now CA $1,733 per person
CA $1,733
per person
Sep 3 - Sep 7
found 13 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9/10 Wonderful! (3,130 reviews)
Nice staff; decent breakfast buffet; for being in the Times Square are of NYC, I think it is a good value.

Reviewed on Jul 19, 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was CA $1,970, price is now CA $1,328 per person
CA $1,328
per person
Aug 31 - Sep 4
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to New York (JFK)
9.2/10 Wonderful! (3,746 reviews)

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Price was CA $4,362, price is now CA $2,966 per person
CA $2,966
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to New York (JFK)
9/10 Wonderful! (1,002 reviews)

Ready to book your vacation to Chelsea?

 

Choose your dates

Chelsea 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 $154 per night from Aug 20 to Aug 21
CA $154
CA $179 total
Aug 20 - Aug 21
includes taxes & fees
9/10 Wonderful! (1,005 reviews)
"Hotel staff was great. Breakfast was great. Was put in a room where the AC did not work. This was actually the second Hyatt house that I stayed at within a few days of each other Where our AC in the room did not work on days that were extremely hot. They seem to have these sensor systems that only ..."

Reviewed on Jul 20, 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 $132 per night from Jul 28 to Jul 29
CA $132
CA $153 total
Jul 28 - Jul 29
includes taxes & fees
8.4/10 Very good! (176 reviews)
"The room was fairly clean. I found a hair in the bedsheets. They do not clean the room every day. I needed extra towels and it took me hunting down housekeeping to get it. The bathroom is too small. The bathroom sink is in the room not the bathroom. Breakfast was good. Bagels were good after toasting. ..."

Reviewed on Jul 19, 2026

Spark by Hilton Fishkill
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive Bear Mountain NY
Fully refundableReserve now, pay when you stay
The price is CA $206 per night from Jul 28 to Jul 29
CA $206
CA $254 total
Jul 28 - Jul 29
includes taxes & fees
8.4/10 Very good! (1,013 reviews)
"Wonderful old feeling with many available activities. Front desk staff was amazing."

Reviewed on Jul 19, 2026

Overlook Lodge at Bear Mountain
See all 784 properties in Chelsea
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
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Frequently asked questions

How much does a Chelsea vacation package cost?
You can snap up a vacation package to this top destination from CA $942 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.