Uppingham Vacations from $1,282

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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.
Cosy 2BR House on Quiet Street

Cosy 2BR House on Quiet Street

2 out of 5
Price was $1,331, price is now $1,282 per person
$1,282
per person
Mar 6 - Mar 8
found 11 hours ago
Roundtrip flight included
Washington (IAD) to East Midlands (EMA)
No reviews
voco Leicester by IHG

voco Leicester by IHG

4 out of 5
Price was $2,369, price is now $1,400 per person
$1,400
per person
Mar 2 - Mar 7
found 2 hours ago
Roundtrip non-stop flight included
Boise (BOI) to East Midlands (EMA)
9/10 Wonderful! (734 reviews)
This was a last minute booking after we decided to go to a gig at the O2 Academy. It was perfectly located, the staff were friendly, the room was clean, the bed extremely comfortable and the shower excellent. Couldn’t fault the stay or the hotel.

Reviewed on Jan 17, 2026

Stylish 1BR Flat Next to Hockley

Stylish 1BR Flat Next to Hockley

2 out of 5
Nottingham City Centre
Price was $1,359, price is now $1,300 per person
$1,300
per person
Mar 6 - Mar 8
found 11 hours ago
Roundtrip flight included
Washington (IAD) to East Midlands (EMA)
No reviews
St Mary's Quarters

St Mary's Quarters

4 out of 5
Nottingham City Centre
Price was $1,413, price is now $1,356 per person
$1,356
per person
Mar 6 - Mar 8
found 11 hours ago
Roundtrip flight included
Washington (IAD) to East Midlands (EMA)
9.6/10 Exceptional! (19 reviews)
Very spacious and a great location.

Reviewed on Jan 12, 2026

Comfy 3BR Flat on Quiet Street

Comfy 3BR Flat on Quiet Street

2 out of 5
Price was $1,370, price is now $1,316 per person
$1,316
per person
Mar 6 - Mar 8
found 11 hours ago
Roundtrip flight included
Washington (IAD) to East Midlands (EMA)
No reviews
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Discover the most popular places to visit in Uppingham

Rutland waters September 18

Rutland Water Nature Reserve

Commune with nature and explore the great outdoors at Rutland Water Nature Reserve during your travels in Oakham. Check out the lively bars or top-notch restaurants in this relaxing area.

Rutland Water Nature Reserve

Normanton Church

Normanton Church is just one of the places to see in Edith Weston, so why not enjoy the other things to explore during your travels? Check out the lively bars or top-notch restaurants in this relaxing area.

Normanton Church

The Rutland Falconry and Owl Centre

Enjoy an outing to The Rutland Falconry and Owl Centre during your stay in Burley. Amble around this quaint area's picturesque gardens and enjoy its lively bars.

The Rutland Falconry and Owl Centre

Uppingham Hotel Deals

The Crown

The Crown

3 out of 5
19 High Street East Oakham England
Fully refundableReserve now, pay when you stay
$117 nightly
The price is $141 total per night from Jan 26 to Jan 27
$141 total
Jan 26 - Jan 27
Total with taxes and fees
8.6/10 Excellent! (165 reviews)
Friendly helpful staff

Reviewed on Dec 26, 2025

The Crown
Leicester Marriott Hotel

Leicester Marriott Hotel

4 out of 5
Smith Way, Grove Park, Enderby Leicester England
Fully refundableReserve now, pay when you stay
$77 nightly
The price is $93 total per night from Jan 24 to Jan 25
$93 total
Jan 24 - Jan 25
Total with taxes and fees
8.6/10 Excellent! (1,000 reviews)
Check in was very good, the room was brilliant in a great location. The only downside was the breakfast, plates were cold, the cooked food was cold and the bread for toast was very stale.

Reviewed on Jan 11, 2026

Leicester Marriott Hotel
Novotel Leicester

Novotel Leicester

4 out of 5
2 Great Central Street Leicester England
Fully refundableReserve now, pay when you stay
$86 nightly
The price is $103 total per night from Jan 25 to Jan 26
$103 total
Jan 25 - Jan 26
Total with taxes and fees
9/10 Wonderful! (979 reviews)
The hotel is in a good location on the edge of the city centre and is easy to reach by car.

Reviewed on Jan 17, 2026

Novotel Leicester
See all 1,208 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 $1,282 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.