Gregory County Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$134 when you book a flight and hotel together*

  • Find the right fit

    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

The Annual Holiday Sale

Members save up to 40% on hotels. Plan this year’s big trip and save.
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Top hotels in Gregory County

Holiday Inn Express & Suites Winner by IHG

Holiday Inn Express & Suites Winner by IHG

2.5 out of 5
1360 E Highway 44 Winner SD
Fully refundable
The price is S$120 per night from 23 Mar to 24 Mar
S$120
23 Mar - 24 Mar
includes taxes & fees
8.8/10 Excellent! (353 reviews)
Everything was great!!!

Reviewed on 15 Feb, 2026

Holiday Inn Express & Suites Winner by IHG
Super 8 by Wyndham Winner SD

Super 8 by Wyndham Winner SD

2 out of 5
902 E Highway 44 Winner SD
Fully refundableReserve now, pay when you stay
The price is S$97 per night from 13 Mar to 14 Mar
S$97
13 Mar - 14 Mar
includes taxes & fees
Super 8 by Wyndham Winner SD
Wagner Lakeside Motel

Wagner Lakeside Motel

2.5 out of 5
710 W Hwy 46 Wagner SD
Fully refundableReserve now, pay when you stay
The price is S$121 per night from 27 Feb to 28 Feb
S$121
27 Feb - 28 Feb
includes taxes & fees
6.4/10 (175 reviews)
Room was okay. We had the queen room with the hottub. It was.. okay. The breakfast (as stated) never included a hot selection. Just a DIY waffel and frosted flakes. I think there were some other random premade stuff but we just left. Room was good. Breakfast sucked. For $140 you could atleast give ...

Reviewed on 16 Feb, 2026

Wagner Lakeside Motel
See all 80 properties in Gregory County
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 County holiday package cost?
From as low as . Yes, you read that correctly. Our Gregory County holiday packages are the best way to make your budget last longer. Bundle your preferred hotels, flights and car rentals and get out and explore this fabulous destination.
How do I get a cheap travel package to Gregory County?
One of the easiest ways to save money (and time) is to bundle your bookings with Expedia. Hotels, flights, rental cars and activities — we've got them all. Choose a combination that best suits you and see your savings pile up. We know a package deal is never a one-size-fits-all. That's why we offer over 550 airlines and 1,000,000 hotels around the globe, which lets you customize your Gregory County adventure.
What are the top hotels in Gregory County?
When it comes to properties in Bonesteel, Whetstone Bay Lodge Room 8 and Whetstone Bay Lodge Room 6 are two excellent options. If you're also spending time in Gregory, Whetstone Bay Lodge Room 7 and Whetstone Bay Lodge Room 2 are waiting to welcome you.
How far in advance should I book my Gregory County holiday?
Reserving your seat early with Expedia means one less thing to worry about. Most air carriers advertise tickets up to 12 months prior to take off. Generally, this is the cheapest time to book. If circumstances have left you booking late, great deals to Gregory County occasionally appear in the weeks leading up to departure.
What does an Expedia Gregory County travel package include?
With Expedia, you can choose any combination of flights, hotels and car rentals to create your perfect Gregory County travel package. Once you've made your booking, you can add on all the fun stuff like tours and experiences. Remember — the more you bundle, the more you'll save!
What should I know before booking a Gregory County travel package?
A package can be more affordable than individually booking everything you need for your escape. For example, combine your hotels, flights and rental cars and save a packet. Whatever your holiday goals are, you're bound to find a package to suit your budget.
Can I choose my airline with a Gregory County Expedia holiday package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines all over the world. Our packages give you the freedom to take your pick of available flights, hotels and activities that suit you.
If I'm not able to travel, can I cancel my Gregory County holiday package?
You can. We realise life happens, so we're happy to help if you have to make changes to your Gregory County holiday package. It may be possible to cancel or amend your itinerary for free if you've booked in the last 24 hours. Your airline, hotel or car rental company may impose a fee if you booked more than 24 hours ago. Visit our Customer Service Portal for further information. Also, check your itinerary for the finer details on change fees.

* 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.