Oakham Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to £335 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

    Packages with flights are ATOL protected

Your Oakham Holiday

Planning your next epic escape is a breeze with a Oakham holiday package. The neighbourhood of Webster Square, which is great for cycling, makes a good starting point to discover the delights of this city. If your trip to Oakham includes some sightseeing, visit major attractions such as Rutland State Park, Barre Common District and Barre Historical Society. Expedia will help you escape the everyday. Tailor your holiday to Oakham to suit your style of travel, whatever that may be.

Oakham Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Worcester Regional Airport (ORH)
Population
1,700
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
Hardwick Vineyard and Winery, Wachusett Mountain State Reservation and Rutland State Park

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 £74 per night from 11 Aug to 12 Aug
£74
11 Aug - 12 Aug
includes taxes & fees
8.8/10 Excellent! (1,463 reviews)
"We loved our stay! We were traveling from Michigan to Maine and only had the opportunity to stay one night, but we had a wonderful meal at the tavern on site. The bakery options were loved by my children, and we all enjoyed walking the grounds. Would definitely return!"

Reviewed on 10 Aug 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 £99 per night from 11 Aug to 12 Aug
£99
11 Aug - 12 Aug
includes taxes & fees
9/10 Wonderful! (1,267 reviews)
Wellsworth Hotel
"Wonderful hotel!! Historic and beautiful!! Friendly staff!! Excellent on-site restaurant! Definitely will be staying there in the future!!"

Reviewed on 9 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! (1,000 reviews)
"i travel weekly in central/western MA and the colonial is always LOVELY!"

Reviewed on 5 Aug 2025

Get rates
The Colonial Hotel
See all 284 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does an Oakham travel package cost?
Our Oakham travel packages, which begin from just , are an ideal way to save big. Choose your favourite flights, hotels and rental cars to create a personalized itinerary.
If I'm not able to travel, can I cancel my Oakham travel package?
Plans can change suddenly, so yes, you can. You may be able to cancel and rebook your Oakham travel package for free if you've booked in the last 24 hours. For older bookings, you can still cancel or make changes, but your car rental company, airline or hotel may impose a charge. Looking for more information? Look up our Customer Service Portal. We'll help make sure your getaway goes off without a hitch.
How do I get a cheap travel package to Oakham?
Browse and book everything all in one place with our Oakham travel packages. We have incredible bargains on hotels, flights and more that'll keep your pocketbook happy and your adventurous spirit full. And, with more than 550 partner airlines and 1,000,000 hotels throughout the world to select from, you have countless opportunities to mix and match as you want.
Does Expedia offer Book Now, Pay Later Oakham holidays?
Your bank balance shouldn't prevent you from escaping on holiday, so Expedia has devised a solution to help. Now that we've teamed up with online lender Klarna, it's easier than ever to book a fabulous getaway without exhausting your savings. Klarna offers flexible payment options at checkout that take the stress out of budgeting for your break. Check out these flexible payment options:

  • Pay monthly holidays: Realise your holiday dreams sooner with Klarna's manageable monthly instalment plans. If making bite-sized repayments each month sounds right for you, choose this option at checkout.
  • Pay in instalments holidays: If you want to pay for your escape across multiple transactions, holidays paid in instalments might be the right option for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: Pressing the "book now" button is easier with this payment option. Put down a small deposit on your escape and then get on your way.

Where should I stay in Oakham?
If you'll be visiting Rutland State Park, maximize your time sightseeing and book a hotel nearby. It's one of the most popular attractions in this area.
What are the top hotels in Oakham?
Get your escape off to a good start by booking a room at Boston Park Plaza. It's one of most sought-after properties in Oakham. Another cosy option is Embassy Suites Boston Logan Airport.
How far in advance should I book my Oakham holiday?
Travellers are normally able to look up international flights on Expedia up to a year in advance of departure. Booking last minute? With a stroke of luck, it's still possible to score a cheap ticket only weeks before your journey.
What does an Expedia Oakham travel package include?
Packages include flights, hotels and rental cars, but you can mix and match them to create your ideal Oakham escape. You can also add on fun stuff like activities and experiences once you've made your booking. You're in charge! When you bundle your bookings with Expedia, you'll get discounts you won't find anywhere else.
What should I know before booking an Oakham travel package?
A travel package can be easier on the credit card than separately booking everything you need for your adventure. For example, combine your flights, hotels and rental cars and save a packet. Whatever your holiday goals are, you'll find a package that suits your budget.
Can I choose my airline with an Oakham Expedia travel package?
Yes, so take your pick! We have access to over 550 partner airlines across the globe, so you can customize your Oakham trip according to your travel needs.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.