Uppingham Vacations from $986

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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.
Best Western Plus Ullesthorpe Court Hotel & Golf Club

Best Western Plus Ullesthorpe Court Hotel & Golf Club

4 out of 5
Price was $1,113, price is now $986 per person
$986
per person
Nov 23 - Nov 29
found 9 hours ago
Roundtrip flight included
New York (NYC) to East Midlands (EMA)
8.6/10 Excellent! (460 reviews)
Initially not easy to familiarise with the layout of rooms an facilities.

Reviewed on Aug 22, 2025

Bushrah House

Bushrah House

2 out of 5
Price was $1,503, price is now $1,470 per person
$1,470
per person
Nov 9 - Nov 10
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to East Midlands (EMA)
No reviews
Hart's Hotel

Hart's Hotel

4 out of 5
Nottingham City Centre
Price was $1,374, price is now $1,349 per person
$1,349
per person
Nov 9 - Nov 10
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to East Midlands (EMA)
9.4/10 Exceptional! (478 reviews)
As always wonderful stay

Reviewed on Sep 12, 2025

The Old School House & Rooms- The Lace Market

The Old School House & Rooms- The Lace Market

3.5 out of 5
Nottingham City Centre
Price was $1,413, price is now $1,394 per person
$1,394
per person
Nov 9 - Nov 10
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to East Midlands (EMA)
10/10 Exceptional! (2 reviews)
St Mary's Quarters

St Mary's Quarters

4 out of 5
Nottingham City Centre
Price was $1,347, price is now $1,330 per person
$1,330
per person
Nov 9 - Nov 10
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to East Midlands (EMA)
9.8/10 Exceptional! (12 reviews)
Only thing that would make it better is a hot tub on the terrace

Reviewed on Jul 13, 2025

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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 quaint area.

Rutland Water Nature Reserve
10/10 😻

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

Oakham Castle

Oakham Castle is just one of the places to see in Oakham, so why not enjoy the other things to explore during your travels? Amble around this relaxing area's picturesque gardens and enjoy its top-notch restaurants.

Oakham Castle

Uppingham Hotel Deals

The Crown

The Crown

3 out of 5
19 High Street East, Oakham, England
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $143 total per night from Sep 21 to Sep 22
$143 total
Sep 21 - Sep 22
Total with taxes and fees
8.6/10 Excellent! (161 reviews)
"Bed was very hard and the shower cubicle was a little tired. Breakfasts were very enjoyable."

Reviewed on Aug 18, 2025

The Crown
voco Leicester by IHG

voco Leicester by IHG

4 out of 5
101 Welford Road, Leicester, England
Fully refundableReserve now, pay when you stay
$72 nightly
The price is $86 total per night from Sep 21 to Sep 22
$86 total
Sep 21 - Sep 22
Total with taxes and fees
9/10 Wonderful! (647 reviews)
"Bed is cosy. Air conditioning works smoothly."

Reviewed on Sep 15, 2025

voco Leicester by IHG
The Belmont Hotel

The Belmont Hotel

4 out of 5
20 De Montfort St, Leicester, England
Fully refundableReserve now, pay when you stay
$77 nightly
The price is $93 total per night from Oct 19 to Oct 20
$93 total
Oct 19 - Oct 20
Total with taxes and fees
9.2/10 Wonderful! (1,007 reviews)
Always given a good welcome at Belmont
"Always given a good welcome. Comfortable furniture and generally clean. Room seemed a bit old fashioned and a bit of mould in shower otherwise 5 star. Lovely breakfast."

Reviewed on Sep 15, 2025

The Belmont Hotel
See all 1,153 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.

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Frequently asked questions

How much does an Uppingham vacation package cost?
You'll find cheap prices from $986 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.