Plan your trip
Get more, spend less whenever you see Bundle & Save deals
Earn OneKeyCash on all your eligible bookings
We are not like the others - we include taxes and fees
Check prices for these dates, December 12 – 13, 2026
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.
Stroll along the picturesque waterfront trails or explore the charming downtown filled with boutique shops and cafes. Golf enthusiasts can tee off at the renowned Glen Abbey course, while culture lovers enjoy performances at the Oakville Centre.
Prices for B&Bs in Oakville often vary, but you can find a great deal from $136 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Oakville B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
The best time to book a B&B in Oakville is during the vibrant summer months of June through August, when the town comes alive with outdoor events and activities. This period is particularly appealing to travelers who enjoy exploring local wineries and attending the popular summer festivals that showcase Oakville's rich culture and community spirit. With temperatures typically ranging from the mid-70s to low 80s Fahrenheit, the warm climate is great for leisurely strolls by the waterfront or tasting exquisite local wines.
July stands out as the most popular month to visit, offering a bustling atmosphere filled with fellow adventurers and opportunities for sightseeing. You can enjoy the scenic beauty of the region, with lush landscapes and the picturesque backdrop of Lake Ontario enhancing your stay. Attend outdoor concerts or local farmers' markets, which provide a taste of the community's vibrant life.
If you're looking for a more budget-friendly option, consider visiting in November. This shoulder month provides a quieter experience, allowing you to appreciate the serene beauty of Oakville without the crowds. While the weather may be cooler, it’s an ideal time for cozy indoor activities, such as wine tastings and exploring local shops.
Every Oakville B&B has its own unique feel. Whether it’s a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Oakville B&Bs.