Chelsea Vacation Packages

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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.
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was CA $1,179, price is now CA $697 per person
CA $697
per person
Oct 6 - Oct 9
found 15 hours ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9.2/10 Wonderful! (1,003 reviews)
Very large room, well maintained hotel, friendly helpful staff.

Reviewed on Aug. 25, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $2,629, price is now CA $1,541 per person
CA $1,541
per person
Oct 3 - Oct 5
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,009 reviews)
Wonderful room and staff. The Brooklyn Bridge view was amazing.

Reviewed on Aug. 21, 2025

The Luxury Collection Hotel Manhattan Midtown

The Luxury Collection Hotel Manhattan Midtown

5 out of 5
Manhattan
Price was CA $1,798, price is now CA $1,101 per person
CA $1,101
per person
Nov 7 - Nov 10
found 18 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,004 reviews)
Great location, complimentary water which saved us a lot of money on bottled water! Front desk hooked us up with an upgrade. We requested to have all snacks and drinks removed from our son's room and they didn't do it. He got into the snacks and we were charged $160 super annoying, we knew he would get into the snacks and would have appreciated them doing us a solid by removing the $20 gummy bears

Reviewed on Aug. 17, 2025

Hyatt Regency Jersey City on the Hudson

Hyatt Regency Jersey City on the Hudson

4 out of 5
Downtown Jersey City
Price was CA $1,572, price is now CA $974 per person
CA $974
per person
Oct 30 - Nov 2
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
8.2/10 Very Good! (1,466 reviews)
This hotel had a beautiful view of the Hudson and the city. It was super convenient to the PATH station and parking garage.

Reviewed on Aug. 25, 2025

Omni Berkshire Place

Omni Berkshire Place

4 out of 5
Manhattan
Price was CA $2,788, price is now CA $1,802 per person
CA $1,802
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (1,951 reviews)
This stay was very nice. Staff were amazing and helpful. Valet parking was smooth and easy. The hotel room was large and very clean. We requested a refrigerator and had one in our room when we arrived. Room was quiet and beds comfortable. Would definitely recommend.

Reviewed on Aug. 26, 2025

Ready to book your vacation to Chelsea?

 

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Chelsea Hotel Deals

The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
5 Lakeside Rd, Newburgh, NY
The price is CA $128 per night from Sep 2 to Sep 3
CA $128
CA $151 total
Sep 2 - Sep 3
includes taxes & fees
7.2/10 Good! (522 reviews)
"I enjoyed the location. The place was clean and employees were very pleasant"

Reviewed on Aug. 21, 2025

The Crossroads Hotel, Newburgh
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive, Bear Mountain State Park, Bear Mountain, NY
The price is CA $215 per night from Sep 25 to Sep 26
CA $215
CA $244 total
Sep 25 - Sep 26
includes taxes & fees
8.2/10 Very Good! (1,008 reviews)
"The Overlook Lodge is a wonderful property nestled in the woods and yet close to the Inn for dining. Our room was spacious and the beds were very comfortable."

Reviewed on Aug. 23, 2025

Overlook Lodge at Bear Mountain
Wildflower Farms, Auberge Resorts Collection

Wildflower Farms, Auberge Resorts Collection

5 out of 5
2702 Main St, Gardiner, NY
The price is CA $1,398 per night from Sep 22 to Sep 23
CA $1,398
CA $1,626 total
Sep 22 - Sep 23
includes taxes & fees
9.4/10 Exceptional! (52 reviews)
"Such a dreamy escape. The staff is excellent, friendly, and always ready to help. The rooms are serene and comfortable. Amazing spa and spa staff. Restaurant is also top-notch"

Reviewed on May 15, 2025

Wildflower Farms, Auberge Resorts Collection
See all 740 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 $697 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.