Skip to content
300+ stays

Stays in Windham

Enter dates and number of guests to see the total price per night. Tourism taxes may be added.
Check travel restrictions before booking.
The health and safety of our communities come first. Please follow government guidelines and travel only if it's essential.
SUPERHOST
Tiny house
Private riverside retreat
2 guests1 bedroom1 bed1 bath
Free parkingWifiKitchenHeating
Includes cancellation flexibility
SUPERHOST
Entire guesthouse
1837 Carriage House Duplex 1200 sq.ft. Art studio
2 guests1 bedroom1 bed1 bath
Free parkingWifiKitchenHeating
Includes cancellation flexibility
SUPERHOST
Entire house
Portland ME .Falmouth 1 bed room private entrance
4 guests1 bedroom1 bed1 bath
Free parkingWifiKitchenHeating
Includes cancellation flexibility
SUPERHOST
Entire guesthouse
Cottage on Black Brook Preserve
2 guests1 bedroom1 bed1 bath
Free parkingWifiKitchenHeating
Includes cancellation flexibility
SUPERHOST
Entire guest suite
Waterfront Escape Minutes from Portland
2 guestsStudio1 bed1 bath
Free parkingWifiKitchenHeating
Includes cancellation flexibility
SUPERHOST
Entire apartment
Tranquil Waterfront Apartment-15 miles to Portland
4 guests1 bedroom2 beds1 bath
Free parkingWifiKitchenHeating
SUPERHOST
Private room
Spacious comfy room
2 guests1 bedroom1 bed1.5 baths
Free parkingWifiKitchenHeating
Includes cancellation flexibility
SUPERHOST
Entire cottage
Sunset Haven - Little Sebago Lake
6 guests3 bedrooms5 beds1.5 baths
Free parkingWifiKitchenHeating
Includes cancellation flexibility
SUPERHOST
Entire house
Rustic renovated barn with artist loft and charm
8 guests3 bedrooms3 beds2 baths
Free parkingWifiKitchenHeating
Includes cancellation flexibility
SUPERHOST
Tiny house
The Chickadee House on Pettingill Pond
4 guests1 bedroom2 beds1.5 baths
Free parkingWifiKitchenHeating
Includes cancellation flexibility
SUPERHOST
Private room
Windham Home in Vacationland
3 guests1 bedroom1 bed1 shared bath
Free parkingWifiKitchenHeating
Includes cancellation flexibility
Entire cottage
Beautiful Sebago Lakes Region
6 guests2 bedrooms4 beds2 baths
Free parkingWifiKitchenHeating
Entire house
Close to Freeport attractions.
2 guests1 bedroom2 beds1 bath
Free parkingKitchenHeating
Includes cancellation flexibility
Hotel room
6. Small, but cozy, and Affordable!
1 guest1 bedroom1 bed1 bath
Free parkingWifiKitchenHeating
SUPERHOST
Private room
Cozy bedroom in Gorham
2 guests1 bedroom1 bed1 shared bath
Free parkingWifiKitchen
Includes cancellation flexibility
SUPERHOST
Private room
Beachside Cottage-5 min to Portland (Queen)
2 guests1 bedroom1 bed2 shared baths
Free parkingWifiKitchenHeating
Includes cancellation flexibility
SUPERHOST
Entire apartment
The "No"tel - near Deering Center
4 guests1 bedroom1 bed1 bath
WifiKitchenHeating
Includes cancellation flexibility
Private room
Sunny room in Artistic Portland home dogs welcome!
1 guest1 bedroom1 bed1 shared bath
Free parkingWifiKitchenHeating
Includes cancellation flexibility
SUPERHOST
Entire apartment
BEST location! HUGE 1 bedroom downtown Portland
4 guests1 bedroom1 bed1 bath
WifiKitchenHeating
SUPERHOST
Private room
Comfy queen bed in a spare bedroom.
2 guests1 bedroom1 bed1 private bath
Free parkingWifiKitchenHeating
Includes cancellation flexibility
120 of 300+ places to stay
Enter dates to see full pricing. Additional fees apply. Taxes may be added.