Oakham, MA

Travel Guide

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
$79 nightly
The price is $88 total per night from Oct 19 to Oct 20
$88 total
Oct 19 - Oct 20
Total with taxes and fees
Book a stay at this spa resort in Sturbridge. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in ...
Publick House Historic Inn and Country Motor Lodge
Wellsworth Hotel

Wellsworth Hotel

3 out of 5
14 Mechanic St Southbridge MA
$104 nightly
The price is $117 total per night from Oct 25 to Oct 26
$117 total
Oct 25 - Oct 26
Total with taxes and fees
Book a stay at this business-friendly hotel in Southbridge. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the pool and the helpful staff ...
9.2/10 Wonderful! (1,677 reviews)
"This is our 6th time staying here, we love it. Its our Home away from Home❤️ The amenities are so nice its such a relaxing atmosphere and always a clean hotel stay every time. We are so grateful for this place!"

Reviewed on Oct 1, 2026

Wellsworth Hotel
Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA

3.5 out of 5
150 Great Wolf Dr Fitchburg MA
$187 nightly
The price is $209 total per night from Oct 4 to Oct 5
$209 total
Oct 4 - Oct 5
Total with taxes and fees
Book a stay at this family-friendly resort in Fitchburg. Enjoy 4 indoor pools, free water park access, and room service. Our guests praise the helpful staff ...
Great Wolf Lodge Boston / Fitchburg, MA
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.
Clean & Cozy Private-3 floor_R 2

Clean & Cozy Private-3 floor_R 2

Worcester MA
Stay at this apartment in Worcester. Enjoy laundry facilities and air conditioning. Popular attractions DCU Center and Union Station are located nearby.
Clean & Cozy Private-3 floor_R 2
Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8

Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8

Brimfield MA
Stay at this vacation home in Brimfield. Enjoy free WiFi, a garden, and an in-room coffeemaker. Popular attractions Wales Public Library and Brimfield Public ...
9.2/10 Wonderful! (10 reviews)
"Wonderful little house and property. The hist provided juice, milk, and delicious muffins. Easy access and a very quiet area."

Reviewed on Sep 29, 2026

Little House Inn-Family/Pet friendly Private Home-Brimfield-2 bedroom, sleeps 8
Dove Cabin up in the Trees

Dove Cabin up in the Trees

Holland MA
Stay at this cabin in Holland. Enjoy a sauna, laundry facilities, and an in-room coffeemaker. Popular attractions Quinebaug Woods and Holland Public Library ...
9.8/10 Exceptional! (36 reviews)
"The "cabin in the trees" is the biggest of 6 or so rental cabins on the site of a former camp that is being renovated as a retreat. The owner lives in a house but will not intrude unless you need her. The cabin is funky but comfortable, with several BRs, AC, internet, and a basic kitchen. There is ..."

Reviewed on Aug 23, 2026

Dove Cabin up in the Trees
See all 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.

Frequently asked questions

When is the best time to visit Oakham?
The best time to visit Oakham is from May through July, when the weather is typically mild and ideal for outdoor activities. For travelers seeking fewer crowds and better value, the quieter months of October through December are a good option, offering a more relaxed experience.
Can I book a refundable hotel in Oakham?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Oakham by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Oakham with Expedia?
Expedia makes it easier to plan your Oakham trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Oakham?
The best choice depends on your travel style. Hotels in Oakham can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Oakham trip on Expedia?
Once you've booked your Oakham trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Oakham trip?
Expedia offers customer support before, during, and after your Oakham trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Oakham?
If it's your first trip to Oakham, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Oakham hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Oakham hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

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