Odyssey 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

  • Rest easy

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

Top hotels in Odyssey

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
The price is S$185 per night from 19 Jul to 20 Jul
S$185
19 Jul - 20 Jul
includes taxes & fees
9/10 Wonderful! (1,899 reviews)
"My hotel room had black wallpaper, and was very gloomy. It had two windows, but the courtyard outside had a roof, and very little light trickled in. The beds were comfortable, though. Valet parking was $47 a night, and there was a $30 resort fee per day. So a lot of hidden charges. I am not sur I ..."

Reviewed on 12 Jul, 2026

Historic Inns of Annapolis
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
The price is S$164 per night from 14 Jul to 15 Jul
S$164
14 Jul - 15 Jul
includes taxes & fees
8.6/10 Excellent! (1,036 reviews)
"We attended the concert on July 11th. When we left, I had not eaten my cookie. When we came back we had ants. Not few, tons of them. I called the front desk immediately and we were quickly given another room. It does make me feel good to get that I would say be leary of having snacks in your ..."

Reviewed on 12 Jul, 2026

DoubleTree by Hilton Hotel Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
The price is S$175 per night from 27 Jul to 28 Jul
S$175
27 Jul - 28 Jul
includes taxes & fees
8.8/10 Excellent! (1,020 reviews)
"Menu on internet needs to be updated for restaurant"

Reviewed on 12 Jul, 2026

Crowne Plaza Annapolis by IHG
See all 1,049 properties in Odyssey
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 an Odyssey holiday package cost?
You can snap up a holiday package to this destination on Expedia. However, how much your holiday to Odyssey costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Odyssey?
You can usually find lower rates and better availability in January, February and November. Check out our cheap Odyssey holiday packages and you could get some excellent off-season deals.
How many days is enough for Odyssey?
With a well-planned itinerary, you can easily hit the main Odyssey attractions in a handful of days. But if you prefer to discover lesser-known spots or go on day trips, think about booking your Odyssey holiday for longer.
How to find the best Odyssey package deals?
Begin your search for an Odyssey package deal by entering your travel dates and destination under our "Packages" tab. Then add some filters, like "Property type" and "Popular locations," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal Odyssey package deal straight away, simply play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Odyssey adventure underway.
Is it cheaper to book an Odyssey holiday as a package?
You can enjoy significant savings on your next Odyssey getaway by booking a customised holiday package. Click on the "Package" heading, then select your travel dates and destination to view the best flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday package to Odyssey?
If you have your Odyssey holiday dates locked in, book as early as you can to snap up some fantastic deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous getaways? Our last-minute deals are ideal for travelling on a whim.
How to plan a trip to Odyssey?

  1. Pick your travel dates: The things you plan to do in Odyssey and your preferred season will help you decide when to travel.
  2. Set a budget: Factor in costs like flights, food and transportation when working out how much to save for your trip to Odyssey. Then, select a hotel that works with your budget, whether that's an affordable option or a high-end getaway.
  3. Decide how long to go away for: Now that you're up to speed on Odyssey, you can work out the perfect length of your holiday. Create a rough plan and give yourself enough time to cover everything you want to see.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a customised Odyssey holiday 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. 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.