1. Lake Pointe Inn

- Location: McHenry
- Guest rating: 9.6/10 (Exceptional, 204 reviews)
- Price: $205 nightly, $234 total, Nov 29 - Nov 30, Total with taxes and fees, for Our top choices for Oakland bed & breakfast
- Review: Great place!, by Gina
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Check prices for these dates, December 13 – 14, 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.
Nestled beside Deep Creek Lake, this mountain town offers year-round adventures from skiing to kayaking. Explore the historic downtown where local shops and farm-to-table restaurants welcome you in hiking boots after a day outdoors.

Prices for B&Bs in Oakland often vary, but you can find a great deal from $141 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Oakland 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 Oakland is during the vibrant spring months of March to May. This period sees the city's parks and gardens in full bloom, creating a picturesque setting for outdoor activities and leisurely sightseeing. With temperatures ranging from the mid-50s to mid-70s Fahrenheit, the weather is pleasantly mild, making it ideal for exploring Oakland's diverse neighborhoods and cultural attractions.
As spring unfolds, visitors can enjoy a variety of events, including the popular Oakland Art Murmur, which showcases local artists and galleries, providing a great blend of culture and community. The city's beautiful waterfront, including Lake Merritt, offers opportunities for walking, picnicking, and even kayaking, all while soaking in the stunning views of the surrounding hills.
If you're looking for a more budget-friendly option, consider a visit in December. While this month is quieter, it presents a unique charm with holiday festivities and the chance to experience Oakland's diverse culinary scene without the summer crowds.
Every Oakland 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 Oakland B&Bs.