Oakham Vacations from $647

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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 $734, price is now $647 per person
$647
per person
Dec 21 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Worcester (ORH)
5.4/10 (9 reviews)
this is your every day hotel/motel.

Reviewed on Sep 13, 2025

The Colonial Hotel

The Colonial Hotel

3 out of 5
Price was $959, price is now $832 per person
$832
per person
Dec 21 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Worcester (ORH)
8.8/10 Excellent! (1,011 reviews)
Yes everything was perfect

Reviewed on Nov 10, 2025

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Oakham Hotel Deals

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 Nov 17 to Nov 18
$161 total
Nov 17 - Nov 18
Total with taxes and fees
8.8/10 Excellent! (1,003 reviews)
Property was great

Reviewed on Nov 8, 2025

The Colonial 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
$95 nightly
The price is $106 total per night from Nov 13 to Nov 14
$106 total
Nov 13 - Nov 14
Total with taxes and fees
9/10 Wonderful! (1,540 reviews)
Nice very old place, with all the services. Nice bar, very good restaurant, and a bakery

Reviewed on Nov 9, 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
$107 nightly
The price is $120 total per night from Nov 22 to Nov 23
$120 total
Nov 22 - Nov 23
Total with taxes and fees
9/10 Wonderful! (1,337 reviews)
I loved everything about my short stay!

Reviewed on Nov 12, 2025

Wellsworth Hotel
See all 292 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 $647 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.