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 $1,443, price is now CA $891 per person
CA $891
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to New York (JFK)
8.6/10 Excellent! (2,500 reviews)
Really enjoyed the Q corner room. Small but got the job done. Best for one person. The vouchers on check in were great to buy snacks, beverages, etc. A bit noisy with outside traffic at night. The bathroom fixtures could have used some work such as the toilet paper holder but not the end of the world. The restaurant on site closes at 10:45 am but I ordered good food for delivery nearby. The little coffee bar in the lobby is nice. There is a coffee shop just across the street. Would stay there again. Very close to the Bronx.

Reviewed on Jul 21, 2026

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
Price was CA $7,502, price is now CA $4,308 per person
CA $4,308
per person
Oct 8 - Oct 14
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to New York (JFK)
9.2/10 Wonderful! (685 reviews)

San Carlos Hotel

San Carlos Hotel

4.5 out of 5
Manhattan
Price was CA $1,642, price is now CA $1,037 per person
CA $1,037
per person
Oct 1 - Oct 4
found 9 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.4/10 Exceptional! (1,820 reviews)
Very clean and comfortable room. The staff was exceptionally friendly and helpful.

Reviewed on Jul 20, 2026

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Price was CA $5,678, price is now CA $3,700 per person
CA $3,700
per person
Sep 25 - Sep 30
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to New York (JFK)
9/10 Wonderful! (1,002 reviews)
Always a great stay, convenient location near Central Park and 5th ave.

Reviewed on Jul 21, 2026

The Plaza, A Fairmont Hotel

The Plaza, A Fairmont Hotel

5 out of 5
Manhattan
Price was CA $8,629, price is now CA $5,626 per person
CA $5,626
per person
Oct 8 - Oct 14
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to New York (JFK)
9/10 Wonderful! (1,013 reviews)

Ready to book your vacation to Chelsea?

 

Choose your dates

Chelsea Hotel Deals

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 $133 per night from Aug 5 to Aug 6
CA $133
CA $154 total
Aug 5 - Aug 6
includes taxes & fees
8.4/10 Very good! (182 reviews)
"Perfect stay"

Reviewed on Jul 22, 2026

Spark by Hilton Fishkill
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 $155 per night from Aug 5 to Aug 6
CA $155
CA $180 total
Aug 5 - Aug 6
includes taxes & fees
Hyatt Place Poughkeepsie / Hudson Valley
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive Bear Mountain NY
The price is CA $207 per night from Aug 2 to Aug 3
CA $207
CA $255 total
Aug 2 - Aug 3
includes taxes & fees
8.4/10 Very good! (1,018 reviews)
"I was in the area for a lacrosse camp and stayed in the cottages. The lodge is conveniently located near the Bear Mountain Bridge that’s takes you across the Hudson to quaint towns and local attractions. A drive past the lodge, up to Perkins point, is peaceful and has beautiful views. The area is ..."

Reviewed on Jul 21, 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
All Inclusive Vacations
Beach 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 $891 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.