Oakham Vacations from $357

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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.
The Colonial Hotel

The Colonial Hotel

3 out of 5
per person
Oct 20 - Oct 22
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Worcester (ORH)
8.8/10 Excellent! (1,009 reviews)
Stayed here years ago. The rooms haven't changed much. The rooms are pretty standard, but the lobby, staff and food are all better than most hotels. Maybe a little old school, but I love the look of the hotel. The bed was really comfortable. The event banquet food has always been wonderful. They can handle the volume of plates without affecting the appeal. Great work!

Reviewed on Aug 12, 2025

Trainmasters Inn

Trainmasters Inn

3 out of 5
per person
Oct 24 - Oct 26
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Worcester (ORH)
9.6/10 Exceptional! (355 reviews)
The on the go breakfast was all carbs, just a muffin, orange juice and fruit yogurt. Coffee was good. Dinner at the associated restaurant, steaming tender, was excellent!!

Reviewed on Aug 9, 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
$99 nightly
The price is $111 total per night from Aug 14 to Aug 15
$111 total
Aug 14 - Aug 15
Total includes taxes and fees
8.8/10 Excellent! (1,457 reviews)
"It’s such a unique property and hard to “rate”. The room was extremely dated, but spacious and comfortable for the most part. The property is sprawling and locating our building took a while. There was a wedding there the night we stayed and it really took over…everything. Made for a later and noisier ..."

Reviewed on Aug 12, 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
$125 nightly
The price is $140 total per night from Aug 24 to Aug 25
$140 total
Aug 24 - Aug 25
Total includes taxes and fees
9/10 Wonderful! (1,268 reviews)
"The architecture of the building and how they showed the original use of the building."

Reviewed on Aug 10, 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
$144 nightly
The price is $161 total per night from Aug 25 to Aug 26
$161 total
Aug 25 - Aug 26
Total includes taxes and fees
8.6/10 Excellent! (1,005 reviews)
"Stayed here years ago. The rooms haven't changed much. The rooms are pretty standard, but the lobby, staff and food are all better than most hotels. Maybe a little old school, but I love the look of the hotel. The bed was really comfortable. The event banquet food has always been wonderful. They ..."

Reviewed on Aug 12, 2025

The Colonial Hotel
See all 286 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?
You'll find cheap prices from $357 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.