Uppingham Vacations from $1,488

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Your Uppingham Vacation

The hassle-free way to experience this vibrant city is with a customized Uppingham vacation package. Base yourself in the neighborhood of Foxton, which is good for nature, history and views or go someplace else — our package deals are all about you. If your trip to Uppingham includes a little sightseeing, check out major attractions such as Rutland Water Country Park, Oakham Castle and Normanton Church. No matter your travel plans or the size of your budget, organizing your ultimate tailored Uppingham vacation is a breeze with Expedia.

The Latest Uppingham vacation packages

Price found within the past 48 hours. Click for updated prices.
Silk Hotel

Silk Hotel

$1,488
per person
Oct 28 - Nov 1
found 1 day ago
Roundtrip flight included
New York (NYC) to East Midlands (EMA)
6/10 (1 review)
En-suite and bedroom clean and ideal for business overnight staff

Reviewed on Jul 18, 2026

Browning House by Smart Corporate Stays

Browning House by Smart Corporate Stays

Westcotes
$3,087
per person
Oct 27 - Nov 1
found 1 day ago
Roundtrip flight included
New York (NYC) to East Midlands (EMA)
No reviews
The Firs Luxury Home

The Firs Luxury Home

$2,897
per person
Oct 28 - Nov 1
found 1 day ago
Roundtrip flight included
New York (NYC) to East Midlands (EMA)
10/10 Exceptional! (2 reviews)
OYO Ivy Hotel

OYO Ivy Hotel

$1,521
per person
Oct 27 - Nov 1
found 19 hours ago
Roundtrip flight included
New York (NYC) to East Midlands (EMA)
6.4/10 (145 reviews)
No clean mattress, for I,Robert, got bugs and itchy on legs.

Reviewed on Aug 14, 2026

The Barn Hotel & Spa

The Barn Hotel & Spa

$1,707
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip flight included
New York (NYC) to East Midlands (EMA)
7.4/10 Good! (557 reviews)
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Uppingham Hotel Deals

The Crown

The Crown

19 High Street East Oakham England
$130 nightly
$156 total
Aug 24 - Aug 25
Total with taxes and fees
8.8/10 Excellent! (173 reviews)
"Very hot rooms and ideally windows need to be left open in the summer - breakfast was poor"

Reviewed on Aug 12, 2026

The Crown
voco Leicester by IHG

voco Leicester by IHG

101 Welford Road Leicester England
Fully refundableReserve now, pay when you stay
$67 nightly
$81 total
Aug 30 - Aug 31
Total with taxes and fees
voco Leicester by IHG
Delta Hotels by Marriott Peterborough

Delta Hotels by Marriott Peterborough

Peterborough Business Park Peterborough England
Fully refundableReserve now, pay when you stay
$82 nightly
$98 total
Aug 23 - Aug 24
Total with taxes and fees
9/10 Wonderful! (422 reviews)
"Very nice room on the first floor - spacious, clean and comfortable. The blackout curtains were really good and the room was very quiet. Nice fluffy towels. My only gripe is having to pay £5 a night to park - having already paid for the hotel I object to having to pay extra to park."

Reviewed on Aug 16, 2026

Delta Hotels by Marriott Peterborough
See all 1,375 properties in Uppingham
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 Uppingham Vacation Packages

Uppingham Essential Information

Language
English
Currency
British pounds sterling
Population
4,700
Max Temp Winter
45ºF
Max Temp Summer
70ºF
Top Sights
Oakham Castle, Normanton Church and Barnsdale Gardens

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Frequently asked questions

How much does an Uppingham vacation package cost?
You'll find cheap prices from $1,488 on Expedia for your Uppingham getaway. However, a range of factors like your choice of hotel, the season and length of stay will influence how much your vacation to Uppingham costs.
What are the cheapest months to go to Uppingham?
If you're looking to snag a cheap Uppingham vacation package, consider planning a trip in July, August and October. You'll usually find lower rates on accommodations and flights during these quieter months — perfect for budget-conscious travelers.
How many days is enough for Uppingham?
The ideal duration for your Uppingham vacation depends on what you'd like to see. Usually, a few days to a week will give you enough time to hit all the top sights and discover some hidden spots along the way.
How to find the best Uppingham package deals?
Finding a cheap Uppingham package deal is a breeze with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, add a few filters and see what's available. You can tailor your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Order the results by "Price: low to high" to view the most economical Uppingham package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book an Uppingham vacation as a package?
You can enjoy significant savings on your next Uppingham break by booking a personalized vacation package. Check the "Package" heading, then enter your destination and travel dates to see the best airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Uppingham?
Secure amazing discounts by booking your flights in advance with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for a spur-of-the-moment Uppingham break.
Does Expedia offer Book Now, Pay Later Uppingham vacation packages?
If you're anything like us, you love jet-setting around the world but don't love the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the total cost of your Uppingham vacation across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.