Chelsea Vacations from $553

Book a Hotel + Flight or Car together to unlock savings

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.

The Latest Chelsea vacation packages

Price found within the past 48 hours. Click for updated prices.
Radio Hotel

Radio Hotel

4 out of 5
Manhattan
Save 100% on your flight
Price was $1,080, price is now $553 per person
$553
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.6/10 Excellent! (2,500 reviews)
I had a great time at my stay.

Reviewed on Jul 21, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $6,378, price is now $3,570 per person
$3,570
per person
Sep 24 - Sep 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (1,006 reviews)
Very nice and clean hotel.

Reviewed on Jul 20, 2026

The Wall Street Hotel

The Wall Street Hotel

5 out of 5
Manhattan
Price was $2,292, price is now $1,361 per person
$1,361
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.6/10 Exceptional! (703 reviews)
Be sure to plan for your transportation (e.g. subway, bus, Uber). The hotel assisted in storing our luggage until check-in, and after checkout they stored our luggage until our flight departed. This was very helpful.

Reviewed on Jul 20, 2026

Sound View Greenport

Sound View Greenport

4 out of 5
Save 100% on your flight
Price was $1,204, price is now $722 per person
$722
per person
Sep 21 - Sep 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.4/10 Very Good! (659 reviews)

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was $1,803, price is now $1,086 per person
$1,086
per person
Sep 12 - Sep 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (3,226 reviews)
We had a great time and it was the perfect location for our time in New York.

Reviewed on Jul 21, 2026

Don't see what you're looking for?
See all available trips from Columbus to Chelsea
View all trips

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
$89 nightly
The price is $103 total per night from Aug 11 to Aug 12
$103 total
Aug 11 - Aug 12
Total with taxes and fees
8.4/10 Very Good! (178 reviews)
"Definitely and older property that was renovated. Bare bones rooms. Not terrible but wouldn’t be my first choice in the area next time."

Reviewed on Jul 21, 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
$110 nightly
The price is $128 total per night from Aug 3 to Aug 4
$128 total
Aug 3 - Aug 4
Total with taxes and 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
Fully refundableReserve now, pay when you stay
$142 nightly
The price is $175 total per night from Jul 22 to Jul 23
$175 total
Jul 22 - Jul 23
Total with taxes and fees
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.

Find the Best Chelsea Vacation Packages

Chelsea Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Stewart Intl. Airport (SWF)
Top Sights
SplashDown Beach, Dia Beacon and Chance Theater

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Chelsea vacation package cost?
You'll find cheap prices from $553 on Expedia for your Chelsea escape. However, factors like the season, choice of hotel and length of stay will determine how much your vacation to Chelsea costs.
What are the cheapest months to go to Chelsea?
You can usually find lower rates and better availability in December, January and February. Check out our cheap Chelsea vacation packages and you could score some great off-season discounts.
How many days is enough for Chelsea?
With a well-planned itinerary, you can easily visit the main Chelsea attractions in a handful of days. But if you prefer to discover lesser-known spots or take day trips, think about booking your Chelsea vacation for longer.
How to find the best Chelsea package deals?
Use Expedia's handy filters to help you find some terrific Chelsea package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or browse for Chelsea package deals in the low season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.
Is it cheaper to book a Chelsea vacation as a package?
You can enjoy significant savings on your next Chelsea break by booking a personalized vacation package. Check the "Package" heading, then enter your destination and travel dates to view the best hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Chelsea?
If you're considering an impromptu Chelsea getaway, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can score amazing deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Chelsea vacation packages?
Secure your perfect escape to Chelsea with Expedia's Book Now, Pay Later vacations. No need to save up or hold off until the next payday — we've partnered with online lender Affirm to give you financial flexibility. Our vacation packages with payment plans let you spread the cost across 3, 6 or 12 months. With no hidden or late payment fees, it's easy to stay on budget and snap up cheap deals before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.