Oakham Holidays

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to S$134 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Oakham

Publick House Historic Inn and Country Motor Lodge

Publick House Historic Inn and Country Motor Lodge

2.5 out of 5
277 Main Street (RT 131), Sturbridge, MA
Fully refundableReserve now, pay when you stay
The price is S$128 per night from 4 Aug to 5 Aug
S$128
4 Aug - 5 Aug
includes taxes & fees
8.8/10 Excellent! (1,457 reviews)
"Very dog friendly"

Reviewed on 30 Jul, 2025

Publick House Historic Inn and Country Motor Lodge
Wellsworth Hotel

Wellsworth Hotel

3 out of 5
14 Mechanic St, Southbridge, MA
Fully refundableReserve now, pay when you stay
The price is S$171 per night from 10 Aug to 11 Aug
S$171
10 Aug - 11 Aug
includes taxes & fees
9/10 Wonderful! (1,256 reviews)
"Clean facility, very spacious"

Reviewed on 1 Aug, 2025

Wellsworth Hotel
The Colonial Hotel

The Colonial Hotel

3 out of 5
625 Betty Spring Road, Gardner, MA
Fully refundableReserve now, pay when you stay
8.6/10 Excellent! (1,002 reviews)
"Toilet kept backing up. They issued plunger."

Reviewed on 29 Jul, 2025

Get rates
The Colonial Hotel
See all 280 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.

Frequently asked questions

How much does an Oakham holiday package cost?
You'll find cheap prices on Expedia for your Oakham getaway. However, a range of factors like your choice of hotel, the season and length of stay will determine how much your holiday to Oakham costs.
What are the cheapest months to go to Oakham?
If you're hoping to book a cheap Oakham holiday package, consider visiting in January, February and November. You'll usually find better prices on flights and hotels during these months — perfect for budget-conscious travellers.
How many days is enough for Oakham?
With a well-organised schedule, you can easily hit the most popular Oakham sights in a handful of days. But if you prefer to venture off the beaten track or take day trips, think about booking your Oakham holiday for longer.
How to find the best Oakham package deals?
Use Expedia's filters to find some fabulous Oakham package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or look for Oakham package deals in the off-season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to book your holiday package well in advance.
Is it cheaper to book an Oakham holiday as a package?
You can enjoy significant savings on your next Oakham getaway by booking a customised holiday package. Click on the "Package" heading, then enter your travel dates and destination to view the best hotel and flight prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a holiday package to Oakham?
If you're planning an impromptu Oakham trip, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can land amazing deals on your flights and hotels by booking ahead.
How to plan a trip to Oakham?

  1. Choose your dates: What you want to do in Oakham and your preferred season can help you decide when to travel.
  2. Set your budget: Factor in expenses such as flights, food and transportation when calculating how much to save for your trip to Oakham. Then, pick a property that fits your budget, whether that's a low-cost stay or a more luxurious getaway.
  3. Decide how many days away: Start by listing all the activities and sights you'd like to experience in Oakham. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your accommodation and airfare: After you've settled on your dates and duration, book the right Oakham holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.