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Windham, ME
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Local STR Agent
Local STR Agent

(Prepared for investors, property managers, and prospective STR operators)
Short‑term rentals are not expressly prohibited in the Town of Windham.
The Town’s Land Use Ordinance (LUO) does not contain a standalone “short‑term rental” chapter. Instead, the ordinance regulates lodging activities through existing use categories that can accommodate STR‑type operations:
| Use Category | How an STR Typically Qualifies | |--------------|--------------------------------| | Bed & Breakfast Inn (Sec. 509) | Whole‑unit or limited‑room rentals in the owner’s primary residence. Requires ≤ 3 guest bedrooms, ≤ 8 guests total, breakfast service, and compliance with NFPA 101 Life‑Safety Code. | | Rooming House (Sec. 545) | Rental of individual sleeping rooms to transient guests. Must meet state Rooming‑House licensing and fire‑safety standards. | | Home Occupation 2 (Sec. 524) | Allows renting a portion of a dwelling when the activity is incidental to residential use, provided it meets the Board‑of‑Appeals criteria (e.g., ≤ 20 % floor‑area, no exterior signage). | | Accessory Apartment (Sec. 501) | A secondary dwelling unit on the same lot as the principal residence. May be used for short‑term stays if the unit complies with building, health, and occupancy standards. |
Bottom line: An STR is permitted only when it fits one of the above categories and complies with the performance standards attached to that use. Operating a “stand‑alone” STR that does not meet a listed use would be considered an illegal un‑permitted use.
Windham hosts earn a median $26,929/year with $334 ADR and 54% occupancy.
Top performers pull in $42,610+ per year.
See the full Windham market breakdownVerify Zoning Eligibility
Select the Appropriate Use Category
Obtain Required Permits & Approvals
Implement Safety & Operational Requirements
Market the Property
Maintain Compliance
| Requirement | Source (Town/State
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Windham is a town in Cumberland County, Maine, situated on the eastern shore of Sebago Lake, the second-largest lake in the state. With a population of approximately 18,000, it is one of the larger communities outside the Portland metropolitan area and functions as a gateway to the Lakes Region, the cluster of towns, ponds, and forests that spreads northward and westward from Greater Portland. The town has a relaxed, outdoorsy character, shaped by year-round lake recreation, light commercial development along its Route 302 corridor, and a strong residential population that commutes into Portland. Portland itself sits about fifteen miles to the southeast, a roughly twenty-five-minute drive via the Veteran’s Memorial Bridge and I-295 or US-302, giving Windham convenient access to the city’s restaurants, harbor, and cultural amenities while keeping it anchored in a more suburban and rural setting.
Sebago Lake is the centerpiece of the area and a major draw for visitors year-round. As the deepest and second-largest lake in Maine, it is known for its exceptionally clean water, sandy bottom, and populations of landlocked salmon and lake trout that make it a destination for anglers. The shoreline within Windham includes public beaches, marinas, and campgrounds, and the lake serves as the headwaters of the Presumpscot River. Visitors can swim, kayak, paddleboard, and boat throughout the warmer months, while fall foliage along the lake draws leaf-peepers from across New England.
Just a few minutes west of town, Sebago Lake State Park offers more than 1,300 acres of forest and shoreline with campsites, picnic areas, a swimming beach, and boat launches. The park is one of the most popular state-park destinations in southern Maine and is especially busy in July and August, when families come for the campground, the sandy beach, and easy access to the open water.
The proximity of Windham to Portland is one of its strongest practical advantages. A short drive east brings visitors to the Old Port district, with its working waterfront, cobblestone streets, and dense concentration of restaurants and breweries, and to nearby Cape Elizabeth, where Portland Head Light sits within Fort Williams Park overlooking the Atlantic. Combining a Portland visit with a stay on Sebago Lake is a common pattern for travelers exploring southern Maine, and it broadens the appeal of a Windham base well beyond the immediate shoreline.
For short-term rental investors, Windham offers an appealing mix of year-round demand drivers. Summer vacationers anchor the peak season, drawn by Sebago Lake and the surrounding state parks, while fall foliage, ice fishing, and proximity to Portland’s airports and cruise terminals keep occupancy steadier through the shoulder seasons. The town’s position at the edge of the Lakes Region, combined with quick access to one of New England’s most visited coastal cities, gives it a versatility that few other Cumberland County locations can match.
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