Uppingham Vacations from $2,241

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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.
Mercure Nottingham Sherwood Hotel

Mercure Nottingham Sherwood Hotel

4 out of 5
Price was $2,286, price is now $2,241 per person
$2,241
per person
Dec 28 - Dec 31
found 1 day ago
Roundtrip flight included
New York (JFK) to East Midlands (EMA)
8/10 Very Good! (851 reviews)
Clean room but could do with some better sound proofing

Reviewed on Nov 12, 2026

Browning House by Smart Corporate Stays

Browning House by Smart Corporate Stays

2 out of 5
Westcotes
Price was $2,847, price is now $2,750 per person
$2,750
per person
Dec 29 - Dec 31
found 23 hours ago
Roundtrip flight included
New York (JFK) to East Midlands (EMA)
No reviews

Bestwood Lodge

Bestwood Lodge

3 out of 5
Price was $2,350, price is now $2,288 per person
$2,288
per person
Dec 28 - Dec 31
found 1 day ago
Roundtrip flight included
New York (JFK) to East Midlands (EMA)
7.6/10 Good! (417 reviews)

Quorn Grange Hotel

Quorn Grange Hotel

3 out of 5
Price was $2,342, price is now $2,292 per person
$2,292
per person
Dec 28 - Dec 31
found 1 day ago
Roundtrip flight included
New York (JFK) to East Midlands (EMA)
8.2/10 Very Good! (460 reviews)

The Orchard Hotel & Restaurant

The Orchard Hotel & Restaurant

4 out of 5
Price was $2,372, price is now $2,325 per person
$2,325
per person
Dec 28 - Dec 31
found 1 day ago
Roundtrip flight included
New York (JFK) to East Midlands (EMA)
9.4/10 Exceptional! (1,452 reviews)

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Uppingham Hotel Deals

The Crown

The Crown

3 out of 5
19 High Street East Oakham England
$121 nightly
The price is $146 total per night from Nov 15 to Nov 16
$146 total
Nov 15 - Nov 16
Total with taxes and fees
8.8/10 Excellent! (175 reviews)
"Lovely accommodation in middle of the town, free parking, room large and very comfortable bed. Food in pub was also excellent, and the staff were very friendly and professional. Breakfast was cooked to order band lovely"

Reviewed on Oct 27, 2026

The Crown
voco Leicester by IHG

voco Leicester by IHG

4 out of 5
101 Welford Road Leicester England
$75 nightly
The price is $90 total per night from Dec 14 to Dec 15
$90 total
Dec 14 - Dec 15
Total with taxes and fees
voco Leicester by IHG
3 Bed House - Sleeps 6 - Parking - Wifi

3 Bed House - Sleeps 6 - Parking - Wifi

3 out of 5
Leicester England
Get rates
3 Bed House - Sleeps 6 - Parking - Wifi
See all 1,459 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 $2,241 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.