Oakham Vacations from $425

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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 $457, price is now $425 per person
$425
per person
Nov 21 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Worcester (ORH)
5/10 (8 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 $572, price is now $511 per person
$511
per person
Nov 21 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Worcester (ORH)
8.8/10 Excellent! (1,008 reviews)
It was very expensive for the time of year and area

Reviewed on Sep 26, 2025

Copper Lantern Motor Lodge

Copper Lantern Motor Lodge

2 out of 5
Price was $471, price is now $432 per person
$432
per person
Nov 21 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Worcester (ORH)
8.4/10 Very Good! (152 reviews)
The setting of these rooms is serene and lovely, and I especially liked having a screened, lockable "back door" that opened directly out onto the pond (beautifully misty in the morning) and allowed me to sleep with the door open and fresh cold night air streaming into the room all night long. The owner was also very welcoming and I loved that they manage to be both pet AND allergy friendly by having separate rooms for pets and no pets. A perfect balance.

Reviewed on Sep 27, 2025

Trainmasters Inn

Trainmasters Inn

3 out of 5
Price was $472, price is now $445 per person
$445
per person
Nov 21 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Worcester (ORH)
9.6/10 Exceptional! (364 reviews)
Such a great and interesting place to stay. We absolutely loved it.

Reviewed on Sep 17, 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
$84 nightly
The price is $94 total per night from Sep 29 to Sep 30
$94 total
Sep 29 - Sep 30
Total with taxes and fees
8.8/10 Excellent! (1,524 reviews)
"Our room was really dated and there was a wedding here so it was a lot of partying going on in the middle of the night"

Reviewed on Sep 21, 2025

Publick House Historic Inn and Country Motor Lodge
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 Sep 29 to Sep 30
$161 total
Sep 29 - Sep 30
Total with taxes and fees
8.8/10 Excellent! (1,014 reviews)
Fantastic rest stop.
"Very quiet and spacious with appealing surroundings."

Reviewed on Sep 24, 2025

The Colonial Hotel
Wellsworth Hotel

Wellsworth Hotel

3 out of 5
14 Mechanic St, Southbridge, MA
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $130 total per night from Sep 29 to Sep 30
$130 total
Sep 29 - Sep 30
Total with taxes and fees
9/10 Wonderful! (1,317 reviews)
"This was our second stay this year and we can't wait to make it a third! We love the quiet, clean rooms and historic charm of the hotel. Our 9 year old had a blast in the indoor pool and my husband enjoyed the gym. It was a great time!"

Reviewed on Sep 24, 2025

Wellsworth Hotel
See all 282 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 $425 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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