Oakham Vacations from $308

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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

$308

per person

Nov 12 - Nov 14

found 4 hours ago

Roundtrip flight included

Chicago (CHI) to Worcester (ORH)

7.6/10 Good! (63 reviews)

It didn’t look very good from the entrance but when we pulled into the back which was really the front it looked simple but nice. The staff or owners were lovely and the room and halls were immaculate.

Reviewed on Oct 2, 2026

The Colonial Hotel

$386

per person

Nov 12 - Nov 14

found 4 hours ago

Roundtrip flight included

Chicago (CHI) to Worcester (ORH)

8.8/10 Excellent! (1,007 reviews)

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Oakham Hotel Deals

Publick House Historic Inn and Country Motor Lodge

277 Main Street (RT 131) Sturbridge MA

$79 nightly

$88 total

Oct 19 - Oct 20

Total with taxes and fees

9.2/10 Wonderful! (1,765 reviews)

"All staff were amazingly personal and helpful, low staffing in dining room resulted in food delivered just warm not hot and long delays for food delivery. The only waitress was efficient and apologetic and very sweet. Establishment was great, food good but entrees not hot, room extensive and bake ..."

Reviewed on Oct 6, 2026

Wellsworth Hotel

14 Mechanic St Southbridge MA

$104 nightly

$117 total

Oct 25 - Oct 26

Total with taxes and fees

9.2/10 Wonderful! (1,688 reviews)

"Clean and spacious room with comfy bed made for a great stay!"

Reviewed on Oct 6, 2026

Great Wolf Lodge Boston / Fitchburg, MA

150 Great Wolf Dr Fitchburg MA

$187 nightly

$209 total

Oct 8 - Oct 9

Total with taxes and fees

8.6/10 Excellent! (1,002 reviews)

"El agua del baño salio sicia la aviataion estaba con a rañas"

Reviewed on Oct 5, 2026

See all 356 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 $308 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.