Upton Vacations from $386

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Your Upton Vacation

Well known for its rural countryside and spectacular views, Upton is a fantastic getaway destination. Lock in one of our Upton vacation packages and experience all that this fascinating city has to offer. Love to venture out and explore? Upton Old Town, Red Onion Museum and Cedar Pines Golf Course are a few of the leading places to visit during a trip to Upton. Whoever you're traveling with and whether your budget is big or small, your ultimate Upton vacation is just clicks away with Expedia.

The Latest Upton vacation packages

Price found within the past 48 hours. Click for updated prices.
Howard Johnson by Wyndham Gillette

Howard Johnson by Wyndham Gillette

2 out of 5
Price was $430, price is now $386 per person
$386
per person
Oct 31 - Nov 3
found 3 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Gillette (GCC)
6.8/10 (659 reviews)
Good hotel, I would stay again.

Reviewed on Aug 29, 2025

Summit Suites

Summit Suites

2.5 out of 5
Price was $518, price is now $430 per person
$430
per person
Oct 31 - Nov 3
found 3 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Gillette (GCC)
9/10 Wonderful! (498 reviews)
Very large group of students. Noisy and took over the common area.

Reviewed on Aug 30, 2025

La Quinta Inn & Suites by Wyndham Gillette

La Quinta Inn & Suites by Wyndham Gillette

3 out of 5
Price was $513, price is now $450 per person
$450
per person
Oct 31 - Nov 3
found 3 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Gillette (GCC)
9.6/10 Exceptional! (1,004 reviews)
Nice clean property with easy access. Room was in great shape. Would stay again! Greg.

Reviewed on Aug 29, 2025

Arbuckle Lodge

Arbuckle Lodge

3 out of 5
Price was $540, price is now $477 per person
$477
per person
Oct 31 - Nov 3
found 3 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Gillette (GCC)
9.2/10 Wonderful! (1,008 reviews)
Aside for no fan in bathroom, it was good. Nice breakfast!!

Reviewed on Aug 30, 2025

Wingate by Wyndham Gillette

Wingate by Wyndham Gillette

2.5 out of 5
Price was $497, price is now $445 per person
$445
per person
Oct 31 - Nov 3
found 3 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Gillette (GCC)
8/10 Very Good! (1,003 reviews)
The staff was great. Parking was awesome. I will use this place again

Reviewed on Aug 20, 2025

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Discover the most popular places to visit in Upton

Upton Old Town

You can find out about the history of Upton with a visit to Upton Old Town. Take in the museums while you're in the area.

Upton Old Town

Cedar Pines Golf Course

Enjoy a round of golf in Upton at Cedar Pines Golf Course. Take in the museums while you're in the area.

Cedar Pines Golf Course

Red Onion Museum

You can browse the exhibits at Red Onion Museum, a museum with a storied past, during your trip to Upton. Take in the museums while you're in the area.

Red Onion Museum

Upton Hotel Deals

Iron Creek Inn & Suites

Iron Creek Inn & Suites

2.5 out of 5
100 Buffalo Creek Rd, Upton, WY
Fully refundableReserve now, pay when you stay
$115 nightly
The price is $129 total per night from Sep 7 to Sep 8
$129 total
Sep 7 - Sep 8
Total with taxes and fees
Iron Creek Inn & Suites
Kara Creek Ranch - Rustic 2 Bedroom Cabin #5

Kara Creek Ranch - Rustic 2 Bedroom Cabin #5

Sundance
Get rates
Kara Creek Ranch - Rustic 2 Bedroom Cabin #5
Kara Creek Ranch - 2 bed cabin

Kara Creek Ranch - 2 bed cabin

Sundance
Get rates
Kara Creek Ranch - 2 bed cabin
See all 76 properties in Upton
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 an Upton vacation package cost?
You can pick up a vacation package to this top destination from $386 on Expedia. However, how much your vacation to Upton costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Upton?
If you're hoping to snag a cheap Upton vacation package, consider visiting in February, November and December. You're likely to find better rates on flights and accommodations during these quieter months — perfect for a budget-friendly break.
How many days is enough for Upton?
Usually, a handful of days is enough to see the main sights during your Upton vacation. But if you prefer to have time to unwind or take day trips, consider extending your trip.
Is it worth booking a vacation package to Upton?
Whether you want to explore top attractions like Upton Old Town and Cedar Pines Golf Course on your Upton vacation, or coming for its great culture, history and nature, there's something for everyone here. With so much to see and do, you'll soon find out why so many travelers think Upton is a good vacation destination.
How to find the best Upton package deals?
Use Expedia's handy filters to help you find some terrific Upton package deals. When you start 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 adventure for midweek, or search for Upton package deals in the off-peak season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
Is it cheaper to book an Upton vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll generally score a better deal than booking each component individually. And you'll still have the flexibility to create a tailored Upton vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Upton?
If you have your Upton vacation dates locked in, book as early as you can to snap up some awesome deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous trips? Our last-minute deals are perfect for traveling on a whim.
How to plan a trip to Upton?

  1. Choose when to get away: Check your diary and get packing. Your favorite season and the type of activities on offer will also help you decide when to visit Upton.
  2. Budget wisely: On top of the cost of your accommodations, you should consider other expenses too. These include flights, transportation and food. Also, set aside a little extra for unexpected costs that may come up during your trip to Upton.
  3. Organize your Upton escape with Expedia's trip planning tool: Look for and book hotels and things to do all in one place. You can also collaborate with friends and family to plan an unforgettable trip to Upton together.
  4. Decide how long to go for: Now that you know more about Upton, you can figure out the ideal length of your vacation. Pull together a draft itinerary and allocate enough time to cover everything you want to see.
  5. Combine your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to find an Upton vacation package that brings all your bookings together.
  6. Book activities and experiences ahead of time: Whether it's entrance to a big attraction or a walking tour, you won't have to worry about missing out on Upton's highlights. Find all the incredible things to do in Upton with our dedicated activity guide.

Does Expedia offer Book Now, Pay Later Upton vacation packages?
Set off on your perfect escape to Upton with our Book Now, Pay Later vacations. No need to save like crazy or wait for payday — we've joined forces with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans allow you to split the cost across 3, 6 or 12 months. With no hidden or late payment fees, it's easy to stay on budget and snap up travel deals before they disappear.

Explore a world of travel with Expedia

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.