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Vacation rentals in Windham

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Top-rated vacation rentals in Windham

Guests agree: these stays are highly rated for location, cleanliness, and more.

Cottage on Black Brook Preserve
SUPERHOST
Entire guesthouse · 2 guests · 1 bed · 1 bath
Cottage on Black Brook PreserveThis charming cottage is thoughtfully furnished, it is your home away from home! Clean and cozy, one bedroom with queen size bed and full kitchen. Sit in front of the gas fireplace or on your own private deck overlooking the 105 acres of Black Brook Preserve. Feeling energetic? Take a hike, snow shoe or cross country ski right outside your door. Nearby : Swimming and canoe rentals Fishing.. Lake or River Seacoast Fun Park Portland with 5 star restaurants, shopping, music
Tranquil Waterfront In-Law Apartment
SUPERHOST
Entire rental unit · 4 guests · 2 beds · 1 bath
Tranquil Waterfront In-Law ApartmentSarah's in-law apartment is located on Collins Pond in North Windham, 15 miles to Portland. The backyard fire pit is perfect for relaxation and the picnic table overlooking the pond is a beautiful location to enjoy your morning coffee. Take the kayaks out for a morning venture or the canoe out for the gorgeous sunset! Sarah's one bedroom, one bathroom apartment with private entry, private kitchen, private living space and separate parking will make your stay a tranquil one. Come visit!
Explore Portland from a 18th-Century Victorian
PLUS
Entire residential home · 4 guests · 1 bed · 1 bath
Explore Portland from a 18th-Century Victorian*Covid-Clean* Cook breakfast in a bright kitchen with robust hardwood floors in this calm Victorian home. Sit down at a traditional dining table in an open-plan room featuring vivid wood-paneled walls, serene decor, and a geometric rug with pops of blue.

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Other great vacation rentals in Windham

SUPERHOST
  1. Entire guesthouse
  2. Portland
Private Bungalow w/Hot Tub, Parking
$126 per night
SUPERHOST
  1. Entire guest suite
  2. Windham
Millers Private Studio on Highland Lake
$82 per night
  1. Entire cottage
  2. Raymond
Cozy Cottage, dock and Sebago Lake!
$173 per night
SUPERHOST
  1. Entire guest suite
  2. Portland
Deering Area Suite
$59 per night
SUPERHOST
  1. Entire rental unit
  2. Portland
Safe, quiet, friendly area
$135 per night
SUPERHOST
  1. Yurt
  2. Cumberland
Tree Yurt
$92 per night
PLUS
  1. Entire rental unit
  2. Portland
Elegantly Done Apartment in a Sun-Drenched Corner Lot House
$125 per night
SUPERHOST
  1. Entire guesthouse
  2. Portland
Spacious & Convenient 2 Bedroom w/ Parking
$79 per night
  1. Entire residential home
  2. Westbrook
Majestic Sanctuary!!
$143 per night
SUPERHOST
  1. Entire rental unit
  2. Gorham
Cozy Private 1 Bedroom Apartment - Gorham Village
$87 per night
SUPERHOST
  1. Entire residential home
  2. Windham
Entire Cozy Home 5 Min Walk to Sebago Lake Access
$538 per night
SUPERHOST
  1. Private room
  2. Portland
Close to EVERYthing Portland + great neighborhood
$65 per night