Oakham Vacations from $785

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Your Oakham Vacation

Book a Oakham vacation package and focus on what matters — having fun. No more planning nightmares, just more free time to immerse yourself in the best of this captivating city, such as its rich traditions and rural countryside. Fill your free time with visits to Rutland Water Country Park, Oakham Castle and Barnsdale Gardens, some of the top attractions you shouldn't miss during a trip to Oakham. Check out Expedia's extensive range of travel options and book your ultimate vacation to Oakham today.

The Latest Oakham vacation packages

Price found within the past 48 hours. Click for updated prices.
Best Western Appleby Park Hotel

Best Western Appleby Park Hotel

3 out of 5
Price was $801, price is now $785 per person
$785
per person
Oct 10 - Oct 11
found 7 hours ago
Roundtrip non-stop flight included
New York (JFK) to East Midlands (EMA)
8.2/10 Very Good! (575 reviews)
Room was nice and big very friendly staff and free parking

Reviewed on Aug 17, 2025

Millers Hotel by Greene King Inns

Millers Hotel by Greene King Inns

3 out of 5
Sibson
Price was $790, price is now $785 per person
$785
per person
Oct 10 - Oct 11
found 7 hours ago
Roundtrip non-stop flight included
New York (JFK) to East Midlands (EMA)
8.4/10 Very Good! (605 reviews)
Had a lovely stay ,the room was clean but could do with a freshen up

Reviewed on Jul 28, 2025

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Discover the most popular places to visit in Oakham

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
10/10 😻

Normanton Church

You can learn about the history of Edith Weston with a trip to Normanton Church. 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

Oakham Hotel Deals

Rutland Hall Hotel & Spa

Rutland Hall Hotel & Spa

4 out of 5
North Oakham, Oakham, England
$118 nightly
The price is $141 total per night from Sep 8 to Sep 9
$141 total
Sep 8 - Sep 9
Total with taxes and fees
8/10 Very Good! (958 reviews)
"Very beautiful location. My room was very comfortable and tastefully decorated and the view of the lake was amazing. Staff were very helpful, too."

Reviewed on Aug 17, 2025

Rutland Hall Hotel & Spa
The Barnsdale, Rutland

The Barnsdale, Rutland

4 out of 5
The Avenue Exton, Oakham, England
$137 nightly
The price is $164 total per night from Sep 10 to Sep 11
$164 total
Sep 10 - Sep 11
Total with taxes and fees
8.8/10 Excellent! (645 reviews)
"A lovely hotel with a friendly team of staff. Access to the spa was a great bonus. The food was really good and welcome drink a nice surprise. We ate in the restaurant both nights. The Courtyard was a lovely space to take your drink. Good location. I would recommend a stay at this hotel."

Reviewed on Aug 15, 2025

The Barnsdale, Rutland
Redwings Lodge Uppingham

Redwings Lodge Uppingham

2.5 out of 5
A47 Glaston Road, Morcott, Oakham, England
Fully refundableReserve now, pay when you stay
7.8/10 Good! (737 reviews)
"Nice play to just get your head down for the night. No frills breakfast continental ok. Value for money!"

Reviewed on Aug 18, 2025

Get rates
Redwings Lodge Uppingham
See all 1,695 properties in Oakham
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 Oakham vacation package cost?
You'll find cheap prices from $785 on Expedia for your Oakham escape. However, a range of factors like the hotel choice, length of stay and season will determine how much your vacation to Oakham costs.
What are the cheapest months to go to Oakham?
June, November and December are great times to search for cheap Oakham vacation packages. Traveling in quieter periods means you'll typically find lower prices on hotels and flights.
How many days is enough for Oakham?
When planning your Oakham vacation, a few days will be enough to tour the highlights. Make sure to visit Barnsdale Gardens — it's one of the major attractions in this destination. If you're looking for more adventure, consider basing yourself here and going on some trips from Oakham.
Is it worth booking a vacation package to Oakham?
Whether you want to visit key attractions such as Oakham Castle and Rutland Water Country Park on your Oakham vacation, or coming for its excellent family-friendly attractions, walking trails and culture, there's something for everyone here. With so many things to do, you'll soon learn why so many families think Oakham is a good vacation destination.
How to find the best Oakham package deals?
Bagging a cheap Oakham package deal is easy with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget, apply a few filters and see what's available. You can tweak your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Sort the results by "Price: low to high" to view the most affordable Oakham package deals. Want a simple trick to score 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 Oakham vacation as a package?
You can enjoy significant savings on your next Oakham retreat by booking a customized vacation package. Click on the "Package" heading, then select your travel dates and destination to see the best hotel and flight prices. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Oakham?
If you're considering a spur-of-the-moment Oakham getaway, check out our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can land incredible deals on your hotels and flights by booking well in advance.
How to plan a trip to Oakham?

  1. Choose when to get away: Check your calendar and get packing. Your preferred time of year and the type of activities available will also help you decide when to escape to Oakham.
  2. Budget wisely: Besides the price of your hotel, you'll need to factor in other expenses too. These include food, transportation and flights. Also, set aside a little extra for unexpected expenses that could crop up during your trip to Oakham.
  3. Organize your Oakham getaway with Expedia's trip planning tool: Look for and book accommodations and activities all in one place. You can also collaborate with your group to plan an unforgettable trip to Oakham together.
  4. Decide how many days away: Start by making a list of all the attractions and activities you'd like to get to in Oakham. Then, estimate how long you'll need for each, including any travel time.
  5. Bundle your airfare and accommodations: Once you've nailed down your dates and duration, lock in the ideal Oakham vacation package for you.
  6. Book any day trips or activities: Here's the fun part — locking in everything you want to do and see. Explore some of the exciting things to do in Oakham and reserve your tickets early to save time (and maybe some dollars too!).

Does Expedia offer Book Now, Pay Later Oakham vacation packages?
If you're like us, you love discovering new places but don't love the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the cost of your Oakham trip across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up 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.