Oakham Vacation Packages

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Your Oakham Vacation

Planning your next epic escape is a breeze with a Oakham vacation package. The neighborhood 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 vacation to Oakham to suit your style of travel, whatever that may be.

Top Oakham Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Trainmasters Inn

Trainmasters Inn

3 out of 5
per person
Sep 20 - Sep 23
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Worcester (ORH)
9.6/10 Exceptional! (346 reviews)
I love staying here! It’s fun, clean and the owners are great! Their restaurant is beyond delicious and only a short walk away.

Reviewed on Jul. 13, 2025

The Colonial Hotel

The Colonial Hotel

3 out of 5
per person
Sep 20 - Sep 23
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Worcester (ORH)
8.8/10 Excellent! (1,006 reviews)
I reached out to this property a couple days in advance. Because I was going to be arriving quite late, and wanted to make sure that check in at that time of night was alright. I also inquired about a late check out. The property management responded to me within 24 hours and were able to to accommodate me smoothly. Very kind and friendly staff. Room was clean and spacious. I did not access this for my own needs, but I saw that there were beautiful grounds outside too- very well taken care of.

Reviewed on Jul. 25, 2025

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Oakham Hotel Deals

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 CA $122 per night from Jul 27 to Jul 28
CA $122
CA $136 total
Jul 27 - Jul 28
includes taxes & fees
8.8/10 Excellent! (1,470 reviews)
Good place to stay
"The people were very nice and super accommodating. It is spread out quite a bit but not super hard to navigate. Overall, great value and a nice stay."

Reviewed on Jul. 23, 2025

Publick House Historic Inn and Country Motor Lodge
Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA

3.5 out of 5
150 Great Wolf Dr, Fitchburg, MA
Fully refundable
The price is CA $273 per night from Aug 4 to Aug 5
CA $273
CA $305 total
Aug 4 - Aug 5
includes taxes & fees
8.4/10 Very Good! (1,013 reviews)
"It was pretty good. I’m a germ a phob so the floors when you get out of the pools Linda’s"

Reviewed on Jul. 23, 2025

Great Wolf Lodge Boston / Fitchburg, MA
Wellsworth Hotel

Wellsworth Hotel

3 out of 5
14 Mechanic St, Southbridge, MA
Fully refundableReserve now, pay when you stay
The price is CA $147 per night from Aug 3 to Aug 4
CA $147
CA $164 total
Aug 3 - Aug 4
includes taxes & fees
9/10 Wonderful! (1,256 reviews)
"Great stay"

Reviewed on Jul. 25, 2025

Wellsworth Hotel
See all 279 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?
Offering excellent value package deals from CA $1,328 on Expedia, you'll be thrilled with how little a vacation to Oakham costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Oakham?
If you're hoping to book a cheap Oakham vacation package, consider visiting in January, February and November. You'll usually find better prices on hotels and flights during these quieter months — ideal for budget-conscious travellers.
How many days is enough for Oakham?
The ideal length for your Oakham vacation depends on what you'd like to see. Generally, a handful of days to a week will give you plenty of time to tick off all the top attractions and explore some hidden treasures along the way.
How to find the best Oakham package deals?
Begin your search for an Oakham package deal by entering your destination and preferred trip dates under our "Packages" tab. Then apply some filters, like "Property type" and "Guest rating," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Oakham package deal right away, just change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Oakham getaway off to a flying start.
Is it cheaper to book an Oakham vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking flights and accommodations individually. Better still, you can personalize your Oakham getaway to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Oakham?
If you have your Oakham travel dates finalized, book as early as you can to grab some unbeatable deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are perfect for quick escapes.
How to plan a trip to Oakham?

  1. Pick the ideal time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to go to Oakham.
  2. Calculate your budget: Ensure you have enough money to pay for everything from transportation and food to flights and experiences. Your accommodations will probably be the biggest expense during your trip to Oakham.
  3. Work out your trip length: Think about how long you'd like to spend discovering Oakham. Plan your itinerary so you can get to all the attractions and activities you're interested in at a comfortable pace.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left now is to choose an Oakham vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.