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.
Rent bikes to explore this peaceful island's rocky beaches and historic 1920s inn, where fresh lobster awaits. Take the passenger ferry from Cousins Island for a day trip, then kayak along the quiet coastline or hike wooded trails.
See all hotels in Chebeague Island
Prices for B&Bs in Chebeague Island often vary, but you can find a great deal from $89 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Chebeague Island 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 Chebeague Island is during the summer months, particularly from June to August. This vibrant season draws visitors eager to enjoy the island’s stunning coastal scenery, partake in water activities, and bask in the warm weather, with temperatures typically ranging from the mid-60s to low 80s Fahrenheit.
July stands out as the peak month, where the island comes alive with festivals, outdoor concerts, and bustling local markets. It's an ideal time for families and couples looking to soak in the lively atmosphere, as well as explore the picturesque beaches and charming walking trails that showcase the island’s natural beauty.
For those seeking a more tranquil experience, consider visiting in September. During this time, you can still enjoy pleasant weather, along with the added bonus of fewer crowds. The summer bustle gives way to a quieter charm, allowing for leisurely walks along the shoreline and peaceful moments watching the sunset.
Every Chebeague Island 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 Chebeague Island B&Bs.