Chelsea Vacation Packages

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Top Chelsea Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Cottonwood Airport & Expo Hotel Louisville

Cottonwood Airport & Expo Hotel Louisville

3.5 out of 5
Shively
Price was CA $1,453, price is now CA $1,111 per person
CA $1,111
per person
Aug 21 - Aug 27
found 13 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Louisville (SDF)
8.6/10 Excellent! (1,006 reviews)
Laundry machines were not working, we were staying for a few days to do sports, it would have been nice to clean the uniforms. First night there, several cars were broken into. Right in front of the main door. I was getting ready and watching for the police to respond and it took almost 2 hours for them the show up. Several people were late to the game. Even refs.

Reviewed on Jul 12, 2026

Louisville Marriott Downtown

Louisville Marriott Downtown

4 out of 5
Downtown Louisville
Price was CA $1,701, price is now CA $1,278 per person
CA $1,278
per person
Aug 21 - Aug 27
found 13 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Louisville (SDF)
9/10 Wonderful! (1,000 reviews)
Everything was wonderful

Reviewed on Jul 13, 2026

Hyatt Regency Louisville

Hyatt Regency Louisville

4 out of 5
Downtown Louisville
Price was CA $1,470, price is now CA $1,130 per person
CA $1,130
per person
Aug 21 - Aug 27
found 13 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Louisville (SDF)
8.8/10 Excellent! (1,002 reviews)
There wasn’t a hot tub. Room was big, bed comfortable.

Reviewed on Jul 13, 2026

Moxy Louisville Downtown

Moxy Louisville Downtown

3.5 out of 5
Downtown Louisville
Price was CA $1,409, price is now CA $1,142 per person
CA $1,142
per person
Aug 21 - Aug 27
found 13 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Louisville (SDF)
9.2/10 Wonderful! (789 reviews)
Was a great spot to stay!

Reviewed on Jul 12, 2026

AC Hotel Louisville Downtown

AC Hotel Louisville Downtown

3.5 out of 5
Downtown Louisville
Price was CA $1,378, price is now CA $1,139 per person
CA $1,139
per person
Aug 21 - Aug 27
found 13 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Louisville (SDF)
9.2/10 Wonderful! (670 reviews)
Clean and compensated us for a minor issue of assigning incorrect room. They didn't have to put have us free food and drink passes.

Reviewed on Jul 12, 2026

Ready to book your vacation to Chelsea?

 

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Chelsea Hotel Deals

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 CA $112 per night from Jul 21 to Jul 22
CA $112
CA $129 total
Jul 21 - Jul 22
includes taxes & fees
7/10 Good! (551 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 Jul 7, 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 CA $165 per night from Aug 9 to Aug 10
CA $165
CA $185 total
Aug 9 - Aug 10
includes taxes & fees
8.8/10 Excellent! (717 reviews)
"A decent place to stay for the price. Convenient to dining options. The room was clean and well lit. Water pressure was fine. The mattresses were a bit soft for my liking. There was no hair dryer in the room. 😟 When staff cleans a room there should be a checklist of essentials they sign to indicate ..."

Reviewed on Jul 12, 2026

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 CA $164 per night from Jul 21 to Jul 22
CA $164
CA $189 total
Jul 21 - Jul 22
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 Jul 13, 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.
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Frequently asked questions

How much does a Chelsea vacation package cost?
Offering great value package deals from CA $1,111 on Expedia, you'll be surprised at how little a vacation to Chelsea costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Chelsea?
If you'd like to book a cheap Chelsea vacation package, consider visiting in January, February and March. You'll typically find lower rates on flights and accommodations during these quieter months — perfect for budget-conscious travellers.
How many days is enough for Chelsea?
Usually, a handful of days is enough to go to the main sights during your Chelsea vacation. However, if you prefer to have time to kick back or take day tours, consider extending your trip.
How to find the best Chelsea package deals?
Bagging a cheap Chelsea package deal is easy with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your budget range, add a few filters and browse what's available. You can tweak your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most economical Chelsea package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Chelsea vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll typically get a better deal than booking each component individually. And you'll still enjoy the flexibility to create a tailored Chelsea vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Chelsea?
If you're planning a spontaneous Chelsea trip, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can score terrific deals on your hotels and flights by booking ahead.
How to plan a trip to Chelsea?

  1. Pick the perfect time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to visit Chelsea.
  2. Budget wisely: As well as the price of your accommodations, you should consider other expenses too. These include transportation, flights and food. Also, set aside some extra funds for unexpected expenses that could arise during your trip to Chelsea.
  3. Decide how long to go away for: Now that you know more about Chelsea, you can figure out the right length of your break. Put together a rough itinerary and allocate enough time to cover everything you want to see.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, hotels, car rental and more into a customized Chelsea vacation package.

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.