Chelsea Holidays

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  • Better together

    Save up to S$1,300 when you book a flight and hotel together*

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

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    Plan, book, and manage your trip all in one place

Top hotels in Chelsea

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 S$167 per night from 16 Aug to 17 Aug
S$167
16 Aug - 17 Aug
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
Fully refundableReserve now, pay when you stay
The price is S$213 per night from 2 Aug to 3 Aug
S$213
2 Aug - 3 Aug
includes taxes & fees
8.4/10 Very good! (1,027 reviews)
"We stayed in one of the stone cottages and were given two keys to our room and only one of the two worked. Walls are pretty thin you could hear other people's conversations. The room itself was cozy and clean and has a romantic vibe making it an ideal location for a weekend getaway with your ..."

Reviewed on 27 Jul, 2026

Overlook Lodge at Bear Mountain
DoubleTree by Hilton Poughkeepsie Convention Center

DoubleTree by Hilton Poughkeepsie Convention Center

4 out of 5
40 Civic Center Plz Poughkeepsie NY
Fully refundableReserve now, pay when you stay
The price is S$177 per night from 24 Aug to 25 Aug
S$177
24 Aug - 25 Aug
includes taxes & fees
DoubleTree by Hilton Poughkeepsie Convention Center
See all 777 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.

Frequently asked questions

How much does a Chelsea holiday package cost?
You'll find cheap prices on Expedia for your Chelsea escape. However, factors like the season, choice of hotel and length of stay will determine how much your holiday to Chelsea costs.
What are the cheapest months to go to Chelsea?
You can usually find lower rates and greater availability in January, February and March. Explore our cheap Chelsea holiday packages and you could get some great off-season discounts.
How many days is enough for Chelsea?
With a well-organised itinerary, you can easily hit the most popular Chelsea attractions in a handful of days. But if you'd like to discover hidden gems or go on day tours, think about booking your Chelsea holiday 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 holiday package well in advance.
Is it cheaper to book a Chelsea holiday as a package?
You can enjoy significant savings on your next Chelsea break by booking a personalised holiday 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 holiday 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.
How to plan a trip to Chelsea?

  1. Choose your travel dates: What you want to do in Chelsea and your preferred season will help you decide when to travel.
  2. Budget wisely: As well as the price of your accommodation, you should factor in other expenses. These include transportation, flights and food. Also, set aside some extra funds for unexpected expenses that may arise during your trip to Chelsea.
  3. Set the duration of your trip: Start by listing all the activities and attractions you'd like to experience in Chelsea. Then, estimate how long you'll need for each, including any travel time.
  4. Combine your airfare and accommodation: After you've settled on your trip dates and duration, lock in the perfect Chelsea holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.