Gregory Holidays

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

    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 Gregory

AmericInn by Wyndham Chamberlain - Conference Center
AmericInn by Wyndham Chamberlain - Conference Center
2.5 out of 5
1981 East King Street, Chamberlain, SD
Fully refundableReserve now, pay when you stay
The price is S$211 per night from 10 Aug to 11 Aug
S$211
10 Aug - 11 Aug
includes taxes & fees
8.4/10 Very Good! (1,008 reviews)
"This was such a cozy and personalized AmericInn! We loved the fireplace, the mounted wildlife, and the rooms had new carpet and felt super clean. Also great breakfast in the AM before we left."

Reviewed on 11 Jul, 2025

AmericInn by Wyndham Chamberlain - Conference Center
Howard Johnson Hotel & Suites by Wyndham Oacoma
Howard Johnson Hotel & Suites by Wyndham Oacoma
2 out of 5
203 E Hwy 16, Oacoma, SD
Fully refundableReserve now, pay when you stay
The price is S$179 per night from 20 Jul to 21 Jul
S$179
20 Jul - 21 Jul
includes taxes & fees
8.4/10 Very Good! (1,008 reviews)
"Nothing out of the ordinary, but clean room, bathroom and comfortable bed. Nice and quiet."

Reviewed on 9 Jul, 2025

Howard Johnson Hotel & Suites by Wyndham Oacoma
Arrowwood Resort at Cedar Shore
Arrowwood Resort at Cedar Shore
3 out of 5
1500 Shoreline Drive, Oacoma, SD
Fully refundableReserve now, pay when you stay
The price is S$183 per night from 23 Jul to 24 Jul
S$183
23 Jul - 24 Jul
includes taxes & fees
8.2/10 Very Good! (1,008 reviews)
"Great facilities and room. Staff unhelpful about room readiness "forgetting" to tell us when room was ready causing us to miss the wedding at the facilities we were planning to attend."

Reviewed on 10 Jul, 2025

Arrowwood Resort at Cedar Shore
See all 50 properties in Gregory
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 Gregory holiday package cost?
You'll find cheap prices on Expedia for your Gregory getaway. However, a range of factors like the length of stay, hotel choice and season will influence how much your holiday to Gregory costs.
What are the cheapest months to go to Gregory?
If you're looking to snag a cheap Gregory holiday package, consider planning a trip in January, February and November. You'll typically find better prices on flights and accommodation during these quieter months --- perfect for budget-conscious travellers.
How many days is enough for Gregory?
With a well-organised schedule, you can easily hit the main Gregory attractions in a handful of days. But if you want to discover lesser-known spots or take day trips, consider booking your Gregory holiday for longer.
How to find the best Gregory package deals?
Use Expedia's handy filters to find some terrific Gregory 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 escape for midweek, or browse for Gregory package deals in the off-season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your holiday package as soon as possible.
Is it cheaper to book a Gregory holiday as a package?
An Expedia holiday package could land you significant savings when compared to booking accommodation and flights separately. Better still, you can tailor your Gregory trip to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a holiday package to Gregory?
If you're planning a spur-of-the-moment Gregory 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 land sensational deals on your flights and hotels by booking well in advance.
How to plan a trip to Gregory?

  1. Pick your dates: The things you want to do in Gregory and your preferred season will help you decide when to go.
  2. Set your budget: Consider costs like food, flights and transportation when working out how much to put aside for your trip to Gregory. Then, select a hotel that matches your budget, whether that's a low-cost option or a lavish retreat.
  3. Decide how long to go for: Now that you know more about Gregory, you can figure out the perfect length of your break. Create a draft plan and give yourself enough time to get through everything on your must-do list.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a customised Gregory holiday package.

* 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.