Gregory Vacations from $404

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The Latest Gregory vacation packages

Price found within the past 48 hours. Click for updated prices.
Baymont by Wyndham Pierre

Baymont by Wyndham Pierre

2.5 out of 5
Price was $418, price is now $404 per person
$404
per person
Aug 21 - Aug 23
found 6 hours ago
Roundtrip non-stop flight included
Medford (MFR) to Pierre (PIR)
7.6/10 Good! (1,009 reviews)
No shampoo or ice. Holes on top sheet. Staff blamed owner. Also, leg on chair not stable. It was disappointing but that does explain the somewhat reasonable rate. Finally, the breakfast was low end for a “buffet”…….pre formed eggs and small sausage patties. Only dairy in gallon jugs. Again, not the worst but definitely read reviews before relying on the pretty pictures and flowery descriptions.

Reviewed on Jun 14, 2026

The Outpost Lodge

The Outpost Lodge

3 out of 5
Price was $474, price is now $442 per person
$442
per person
Aug 21 - Aug 23
found 6 hours ago
Roundtrip non-stop flight included
Medford (MFR) to Pierre (PIR)
8.4/10 Very Good! (73 reviews)
No dishes in the kitchen. No wifi. Beautiful lake view. Friendly staff.

Reviewed on Mar 21, 2026

Clubhouse Hotel & Suites Pierre

Clubhouse Hotel & Suites Pierre

3.5 out of 5
Price was $551, price is now $532 per person
$532
per person
Aug 21 - Aug 23
found 6 hours ago
Roundtrip non-stop flight included
Medford (MFR) to Pierre (PIR)
8.6/10 Excellent! (1,008 reviews)
Pool is not useful for adults but hottub is huge

Reviewed on Jun 26, 2026

Ramkota Hotel

Ramkota Hotel

3 out of 5
Price was $459, price is now $446 per person
$446
per person
Aug 21 - Aug 23
found 6 hours ago
Roundtrip non-stop flight included
Medford (MFR) to Pierre (PIR)
7.8/10 Good! (881 reviews)
Very awesome breakfast

Reviewed on Jun 23, 2026

My Place Hotel - Ft. Pierre, SD

My Place Hotel - Ft. Pierre, SD

2.5 out of 5
Price was $491, price is now $491 per person
$491
per person
Aug 21 - Aug 23
found 6 hours ago
Roundtrip non-stop flight included
Medford (MFR) to Pierre (PIR)
8.6/10 Excellent! (301 reviews)
Great area to stay at.

Reviewed on Oct 8, 2025

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Gregory Hotel Deals

Rustic Ridge

Rustic Ridge

Gregory SD
$324 nightly
The price is $340 total per night from Jun 27 to Jun 28
$340 total
Jun 27 - Jun 28
Total with taxes and fees
9.8/10 Exceptional! (6 reviews)
"Great Place"

Reviewed on May 6, 2026

Rustic Ridge
Cedar Shore Resort

Cedar Shore Resort

3 out of 5
1500 Shoreline Drive Oacoma SD
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $158 total per night from Jun 30 to Jul 1
$158 total
Jun 30 - Jul 1
Total with taxes and fees
8.4/10 Very Good! (1,003 reviews)
"Everything was smooth, no issues during the stay"

Reviewed on Jun 26, 2026

Cedar Shore Resort
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
$113 nightly
The price is $124 total per night from Jul 12 to Jul 13
$124 total
Jul 12 - Jul 13
Total with taxes and fees
8.6/10 Excellent! (1,000 reviews)
"We had a short, but great stay! :)"

Reviewed on Jun 23, 2026

Howard Johnson Hotel & Suites by Wyndham Oacoma
See all 75 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.

Find the Best Gregory Vacation Packages

Gregory Essential Information

Language
English
Currency
U.S dollars
Population
1,300
Max Temp Winter
30ºF
Max Temp Summer
85ºF

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Frequently asked questions

How much does a Gregory vacation package cost?
You'll find cheap prices from $404 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 vacation to Gregory costs.
What are the cheapest months to go to Gregory?
October, November and December are the best times to search for cheap Gregory vacation packages. Traveling in quieter periods means you can usually find reduced prices on flights and accommodations.
How many days is enough for Gregory?
The ideal duration of your Gregory vacation depends on what you'd like to see. Generally, a few days to a week will give you time to go to all the main attractions and explore some hidden treasures along the way.
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 vacation package as soon as possible.
Is it cheaper to book a Gregory vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking accommodations 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 vacation 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.
Does Expedia offer Book Now, Pay Later Gregory vacation packages?
Jet off on your ideal getaway to Gregory with Expedia's Book Now, Pay Later vacations. No need to save like crazy or hold off until the next payday — we've partnered with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans let you split the cost across 3, 6 or 12 months. With no late payment fees or hidden charges, you can easily stay on budget and snap up travel deals before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.