Oakham Vacations from $421

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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.

The Latest Oakham vacation packages

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

Gardner Inn

2 out of 5
Price was $445, price is now $421 per person
$421
per person
Jul 24 - Jul 27
found 13 hours ago
Roundtrip flight included
Orlando (ORL) to Worcester (ORH)
5.6/10 (25 reviews)
The staff is friendly and helpful. The room was clean and comfortable

Reviewed on May 2, 2026

The Colonial Hotel

The Colonial Hotel

3 out of 5
Price was $603, price is now $532 per person
$532
per person
Jul 24 - Jul 27
found 13 hours ago
Roundtrip flight included
Orlando (ORL) to Worcester (ORH)
8.8/10 Excellent! (1,001 reviews)
Good food. Water pressure could have been better. Overall, will be booking again.

Reviewed on May 3, 2026

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Oakham Hotel Deals

Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA

3.5 out of 5
150 Great Wolf Dr Fitchburg MA
Fully refundableReserve now, pay when you stay
$179 nightly
The price is $200 total per night from May 5 to May 6
$200 total
May 5 - May 6
Total with taxes and fees
8.6/10 Excellent! (1,004 reviews)
I enjoyed the amenities, but the morning of check out we came up on very disturbing notice of bed bugs in our room. (342). Very disturbing. Notified the staff and Robert handled our belongings by putting them in high heat dryers. Not feeling very comfortable.

Reviewed on May 3, 2026

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
$108 nightly
The price is $121 total per night from May 5 to May 6
$121 total
May 5 - May 6
Total with taxes and fees
9.2/10 Wonderful! (1,494 reviews)
It was a very nice hotel the hot tub was great the only thing I would say is change the mattress they were old and not very comfortable. Other then that it was great.

Reviewed on May 3, 2026

Wellsworth Hotel
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
$89 nightly
The price is $99 total per night from May 5 to May 6
$99 total
May 5 - May 6
Total with taxes and fees
9/10 Wonderful! (1,638 reviews)
We were a little early and room wasn’t quite ready I didn’t mind at all. They were polite and it was ready in 10 minutes. Didn’t use the bar. Parking was very convenient. When asked staff about hiking they had several brochures on many places in the immediate area that turned out to be awesome.

Reviewed on May 3, 2026

Publick House Historic Inn and Country Motor Lodge
See all 317 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
U.S dollars
Closest Airport
Worcester Regional Airport (ORH)
Population
1,700
Top Sights
Hardwick Vineyard and Winery, Wachusett Mountain State Reservation and Rutland State Park

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Frequently asked questions

How much does an Oakham vacation package cost?
You'll find cheap prices from $421 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 vacation to Oakham costs.
What are the cheapest months to go to Oakham?
November, December and January are great times to look for cheap Oakham vacation packages. Traveling in quieter periods means you can typically find reduced prices on flights and accommodations.
How many days is enough for Oakham?
With a well-organized travel plan, you can easily tick off the most popular Oakham sights in a few days. But if you'd like to discover hidden spots or take day trips, consider booking your Oakham vacation 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 vacation package well in advance.
Is it cheaper to book an Oakham vacation as a package?
You can enjoy significant savings on your next Oakham getaway by booking a customized vacation package. Click on the "Package" heading, then enter your travel dates and destination to view the best hotel and flight prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation 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.
Does Expedia offer Book Now, Pay Later Oakham vacation packages?
Your Oakham getaway should be a relaxing escape from your daily routine, not a reason for money worries. So to give you a little more flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.

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