Chelsea Vacations from $401

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, 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.

The Latest Chelsea vacation packages

Price found within the past 48 hours. Click for updated prices.
Radio Hotel
Hotel Riu Plaza New York Times Square
The Inn At Fox Hollow Hotel
1 Hotel Brooklyn Bridge
Eurostars Wall Street
Don't see what you're looking for?
See all available trips from Columbus to Chelsea
View all trips

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.

Chelsea Hotel Deals

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury

2.5 out of 5
60 Centre Dr Central Valley NY
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $117 total per night from Dec 11 to Dec 12
$117 total
Dec 11 - Dec 12
Total with taxes and fees
9.2/10 Wonderful! (1,013 reviews)
It’s a little bit noisy when I turn the heat on

Reviewed on Nov 27, 2025

Hampton Inn Harriman Woodbury
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
$102 nightly
The price is $116 total per night from Dec 16 to Dec 17
$116 total
Dec 16 - Dec 17
Total with taxes and fees
8.2/10 Very Good! (1,018 reviews)
We love coming here. Clean, peaceful, lovely environment. Perfect place for family with small kids.

Reviewed on Nov 24, 2025

Overlook Lodge at Bear Mountain
Hampton Inn & Suites Poughkeepsie

Hampton Inn & Suites Poughkeepsie

2.5 out of 5
2361 South Rd Poughkeepsie NY
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $115 total per night from Dec 6 to Dec 7
$115 total
Dec 6 - Dec 7
Total with taxes and fees
8.8/10 Excellent! (1,006 reviews)
Spotless room

Reviewed on Nov 24, 2025

Hampton Inn & Suites Poughkeepsie
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

Frequently asked questions

How much does a Chelsea vacation package cost?
You'll find cheap prices from $401 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.