Hotels, B&Bs, vacation rentals, and cabins in Winslow. Compare real pricing and availability across all major booking sites.
Biggest hotel and B&B inventory in Maine. Free cancellation on most properties, no-fee booking, and a loyalty program that kicks in after a few stays.
Search Booking.com →Best for whole-house rentals, lakefront cottages, and multi-family trips. Dominates the Maine vacation rental market, especially for waterfront properties.
Search Vrbo →Unique stays, in-town apartments, and budget rooms. Strong urban inventory (Portland, Bangor) and lakeside options.
Search Airbnb →Solid hotel inventory with a "stay 10 nights, get 1 free" rewards program. Good for chain hotels and business travel.
Search Hotels.com →Bundles hotels with flights and car rentals. Good for multi-leg trips and cost comparisons.
Search Expedia →Meta-search across Booking, Expedia, Hotels.com, and more. Use when you want to check rates everywhere at once.
Compare on KAYAK →Check out our full guide to Winslow — covers what to see, where to eat, and local tips from people who actually live here.
Read the Winslow guide →Winslow, Maine has a mix of hotels, B&Bs, and vacation rentals depending on your budget and trip length. Booking.com and Hotels.com cover the hotel inventory; Vrbo and Airbnb cover cottages and vacation rentals. Book 2-3 months ahead for summer (late June through early September) in any tourism-heavy coastal town.
Late May through early October is peak season for most of Maine. September is the best balance of weather, low crowds, and full restaurant availability. Winter visits are mostly for skiing (Bethel, Rangeley) or specific events; many coastal businesses close from November through April.
For summer weekends (June-Labor Day), 2-3 months ahead is the floor. Popular tourism towns like Bar Harbor and Kennebunkport often book out 6+ months for peak weekends. Shoulder season (May, September-October) you can usually book 2-4 weeks ahead. Winter lodging outside ski towns is wide open.
Most Maine towns have a mix of budget and premium lodging. For the lowest rates, search Hotels.com and Booking.com for mid-week stays, consider shoulder season (May, late September), and look at surrounding towns — often a 10-minute drive from a tourism hub cuts the nightly rate dramatically.
Compare lodging across regions and find your best home base.
See all Maine regions →