Oakham Vacations from $990

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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.
Nottingham City Centre by Sunday

Nottingham City Centre by Sunday

4 out of 5
Nottingham City Centre
Price was $1,092, price is now $990 per person
$990
per person
Aug 23 - Aug 28
found 22 hours ago
Roundtrip flight included
New York (NYC) to East Midlands (EMA)
7.8/10 Good! (1,002 reviews)
Ideal location with comfortable rooms and an amazing shower

Reviewed on Jun 20, 2026

Oaklands Hall Hotel Grimsby

Oaklands Hall Hotel Grimsby

3 out of 5
Price was $1,462, price is now $1,275 per person
$1,275
per person
Sep 10 - Sep 15
found 12 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to East Midlands (EMA)
8.6/10 Excellent! (303 reviews)
Very helpful staff and so friendly. Found us a room with aircon -much appreciated during the heatwave. Room had everything you needed. Breakfast was reasonably priced and great.

Reviewed on Jun 30, 2026

Healing Manor Hotel

Healing Manor Hotel

4 out of 5
Price was $1,443, price is now $1,336 per person
$1,336
per person
Sep 10 - Sep 15
found 12 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to East Midlands (EMA)
8.8/10 Excellent! (299 reviews)
No wifi in room was terrible other than that everything okay but no wifi in this day and age is terrible especially when you are paying top dollar

Reviewed on Jun 25, 2026

The White Swan

The White Swan

4 out of 5
Price was $1,282, price is now $1,206 per person
$1,206
per person
Sep 10 - Sep 15
found 12 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to East Midlands (EMA)
9.2/10 Wonderful! (338 reviews)
Brilliant hotel

Reviewed on Jun 30, 2026

Millfields hotel

Millfields hotel

3 out of 5
Price was $1,308, price is now $1,259 per person
$1,259
per person
Sep 10 - Sep 15
found 12 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to East Midlands (EMA)
8.8/10 Excellent! (452 reviews)
Friendly staff and clean rooms.

Reviewed on Jul 2, 2026

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Stay near popular Oakham attractions

A historic building on an island in a body of water, with a seagull flying overhead.
Photo by Tony Hicks
Open Photo by Tony Hicks

Rutland Water Nature Reserve

9.2/10 (240 reviews)
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.
See properties

Oakham Hotel Deals

Redwings Lodge Uppingham

Redwings Lodge Uppingham

2.5 out of 5
A47 Glaston Road Oakham England
Fully refundableReserve now, pay when you stay
$48 nightly
The price is $58 total per night from Jul 5 to Jul 6
$58 total
Jul 5 - Jul 6
Total with taxes and fees
8/10 Very Good! (802 reviews)
"Lovely warm reception when I arrived, which was nice and the staff were very helpful throughout my stay. The outside area around the hotel was very neglected, which didn’t give a great impression but the rooms were very clean, if a little tired and in need of some re-furnishing. For the price paid, ..."

Reviewed on Jun 13, 2026

Redwings Lodge Uppingham
The Barnsdale, Rutland

The Barnsdale, Rutland

4 out of 5
The Avenue, Exton Oakham England
Fully refundableReserve now, pay when you stay
$153 nightly
The price is $183 total per night from Jul 6 to Jul 7
$183 total
Jul 6 - Jul 7
Total with taxes and fees
9/10 Wonderful! (710 reviews)
"Staff were amazing my first room number 9 smelt of damp and they quickly moved me, food amazing, spa amazing will definitely be back x"

Reviewed on Jun 19, 2026

The Barnsdale, Rutland
Rutland Hall Hotel & Spa

Rutland Hall Hotel & Spa

4 out of 5
North Oakham Oakham England
Fully refundableReserve now, pay when you stay
$158 nightly
The price is $190 total per night from Jul 20 to Jul 21
$190 total
Jul 20 - Jul 21
Total with taxes and fees
8.2/10 Very Good! (1,001 reviews)
"Really poor and confusing communication from the staff. Not on the same page as each other and no idea what's going on"

Reviewed on Jun 26, 2026

Rutland Hall Hotel & Spa
See all 1,938 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.

Find the Best Oakham Vacation Packages

Oakham Essential Information

Language
English
Currency
British pounds sterling
Population
10,900
Max Temp Winter
45ºF
Max Temp Summer
65ºF
Top Sights
Rockingham Castle, Oakham Castle and Twinlakes Park

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Frequently asked questions

How much does an Oakham vacation package cost?
You'll find cheap prices from $990 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.