Chelsea Holidays

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    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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Top hotels in Chelsea

Best Way Inn Madison

Best Way Inn Madison

2.5 out of 5
700 Clifty Drive Madison IN
Fully refundableReserve now, pay when you stay
The price is S$117 per night from 16 Jul to 17 Jul
S$117
16 Jul - 17 Jul
includes taxes & fees
7/10 Good! (552 reviews)
"This was one of the few rooms left in town for Madison Regatta 2026. Pretty standard for a pet friendly hotel, we were traveling without our dog, definitely in need of a massive remodel. Front desk had a left over Covid glass in place, so communication required asking for repeats at loud volumes ..."

Reviewed on 7 Jul, 2026

Best Way Inn Madison
Holiday Inn Express & Suites Scottsburg by IHG

Holiday Inn Express & Suites Scottsburg by IHG

2.5 out of 5
200 S Beechwood Ave Scottsburg IN
Fully refundable
The price is S$147 per night from 31 Jul to 1 Aug
S$147
31 Jul - 1 Aug
includes taxes & fees
Holiday Inn Express & Suites Scottsburg by IHG
Hillside Inn

Hillside Inn

2.5 out of 5
831 E Main St Madison IN
Fully refundableReserve now, pay when you stay
The price is S$172 per night from 16 Jul to 17 Jul
S$172
16 Jul - 17 Jul
includes taxes & fees
8.6/10 Excellent! (1,006 reviews)
"Loved the view and the history of this property,,will definitely stay again"

Reviewed on 13 Jul, 2026

Hillside Inn
See all 168 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 break. However, a range of 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?
If you're hoping to book a cheap Chelsea holiday package, consider travelling in January, February and March. You're likely to find lower prices on airfares and hotels during these quieter months — ideal for a budget-friendly break.
How many days is enough for Chelsea?
The ideal length for your Chelsea holiday depends on what you'd like to do. Generally, a handful of days to a week will give you enough time to go to all the leading attractions and discover some hidden gems along the way.
How to find the best Chelsea package deals?
Start your search for a Chelsea package deal by entering your destination and travel dates under our "Packages" tab. Then apply some filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the ideal Chelsea package deal straight away, just play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Chelsea escape off to a flying start.
Is it cheaper to book a Chelsea holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to arranging flights and accommodation individually. Better still, you can personalise your Chelsea getaway to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a holiday package to Chelsea?
If you're considering a spur-of-the-moment Chelsea adventure, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can score terrific deals on your flights and hotels by booking ahead.
How to plan a trip to Chelsea?

  1. Pick your dates: What you plan to do in Chelsea and your favourite season will help you decide when to go.
  2. Set a budget: Factor in expenses like flights, transportation and food when working out how much to put aside for your trip to Chelsea. Then, choose a property that suits your budget, whether that's an affordable option or a high-end getaway.
  3. Set the duration of your trip: Start by making a list of all the activities and attractions you'd like to get to in Chelsea. Then, estimate how long you'll need at each, including any travel time.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to pick a Chelsea holiday package that brings all your bookings together.

Explore a world of travel with Expedia

* 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.