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Windham Holiday Homes

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    $303 Average
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    Don't let other travellers get your favourite Windham area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 19 Rentals in Windham
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    Windham
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Windham
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Windham
    5 Bedrooms, 5 Bathrooms, Sleeps 17 Quick View
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    Windham
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • DVD Player
    • Washer
    • Hot Tub
    • Satellite TV
    • Waterfront
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A real "at the lake" feeling exudes from this charming waterside cottage on inlet to Little Sebago. Lovely waterviews from all windows. Dock and waterside deck with bistro table complete the setting. Launch kayaks from the dock or swim from private gorgeous sandy beach a few steps away. Ideal for...
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    Windham, Maine 04062
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Windham
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Washer
    • Internet Access
    • Parking
    • Air Conditioning
    • Waterfront
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the family vacation of your dreams at this three-bedroom North Windham cottage, a lakefront cabin on the shores of Sebago Lake Basin with a private dock, a screened-in porch with stunning sunset views, and a wonderful location near the heart of town. Perched at the water's edge and surrounded...
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    Windham, Maine 04062
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    Windham
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Satellite TV
    • Washer
    • Grill
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy a memorable family getaway on the shores of Sebago Lake Basin at this five-bedroom Windham cottage, a renovated Maine retreat with a deck that overlooks the lake, an outdoor fireplace, and an expansive piece of property just a few steps from a deeded beach. This charming summer cottage sits...
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    Windham, Maine 04062
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    Windham
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Washer
    • Wi-Fi
    • Balcony
    • DVD Player
    • Grill
    • Terrace
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Built in 2005 on peaceful Little Duck Pond in Windham, Maine, this hidden gem is 10 miles from Portland yet is secluded on a 44-acre spring-fed pond. The property is over an acre with 262 feet of waterfront. A private dirt road leads to a small community of summer homes. 

Our all-season home, just...
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    Windham, Maine 04062
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Windham
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
    • Internet Access
    • Parking
    • Grill
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience the simple joys of summer in Maine at this one-bedroom (plus a loft) Windham cabin, a cozy and atmospheric retreat with lovely views of Sebago Lake Basin, a public dock and mooring for your use near the beach, and a wonderful location just a few steps from a sun-splashed beach....
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    Windham, Maine 04062
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
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    The following rentals are within 15 kilometres of Windham.
    Frye Island
    3 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Outdoor Dining Area
    • Grill
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Waterfront
    • Parking
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stay in our beautiful, lakefront, rustic-elegant log cabin and unwind from the hustle and bustle of life. The cabin is located on Frye Island on Sebago Lake where serenity abounds. Spend a week in this 3 bedroom, 2.5 bath authentic log cabin. This is just the ticket for the rest and relaxation...
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    Frye Island, Maine 04071
    Cabin Holiday Rental - 3 Bedrooms, 3 Bathrooms, Sleeps 5
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    Falmouth
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Patio
    • Housekeeping Included
    • Grill
    • Terrace
    • Central Heating
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Please note: Our checkin time is 3pm and checkout is 11am, but we can often accommodate other arrangements! Andy's Retreat is a comfortable, spacious and convenient home-base to relax and explore Portland & Coastal Maine. We're located right off Exit 53 of the Maine Turnpike, just 15 minutes...
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    Falmouth, Maine 04105
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
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    Family-friendly lakefront house with 3 kitchens, private dock - dogs welcome1 / 46
    (2)Excellent
    Standish
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Internet Access
    • DVD Player
    • Satellite TV
    • Patio
    • Grill
    • Waterfront
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 June 2017
    We had a great time at this home. The views from the lake facing windows and decks are amazing! Awesome sunrises! The sounds of the loons at dusk while sitting by the firepit...
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    About this property
    Your family and friends will love this lakefront Standish home, a dog-friendly retreat on the shores of Watchic Lake! Enjoy lazy afternoons on the water with the help of a private dock, kayaks, a canoe, two decks, and three covered porches. Gorgeously situated directly on the lakefront, this...
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    Standish, Maine 04084
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Gray
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Private Garden
    • Outdoor Dining Area
    • Parking
    • Wi-Fi
    • Waterfront
    • DVD Player
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A charming lake cottage with knotty pine and a big picture window overlooking beautiful Little Sebago Lake. Don't let the approximate two hour drive from Boston or the four mile distance from the highway fool you...you feel as though you are miles away from the hustle and bustle. The sound of the...
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    Gray, Maine 02170
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Falmouth Foreside Maine Contemporary Cottage Home - indoor lap pool, roof deck1 / 29
    (1)Terrible
    Falmouth
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Private Indoor Pool
    • Washer
    • Wi-Fi
    • Central Heating
    • Hot Tub
    • DVD Player
    • Ocean Views
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    5+ Bedrooms, 3 Full Baths Sleeps 10-14 Just up the hill from one of the largest mooring harbors on the East Coast, and across the street from Maine's most famous General Store is this newly completed property designed and built by one of New England's up and coming Architects. Featuring and...
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    Falmouth, Maine 04105
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Standish
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the Beautiful Sebago Lakes Region Enjoy a quiet, serene property on Maine's second biggest lake, all while being only minutes away from an abundance of shopping and attractions The property is close to all the shops in North Windham which is the shopping hub of the area. It is less than...
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    Location Information
    Standish, Maine 04084
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Standish
    6 Bedrooms, 4 Bathrooms, Sleeps 24 Quick View
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    Amenities & Details
    • Washer
    • Porch
    • DVD Player
    • Secure Parking
    • Central Heating
    • Grill
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    470 Bonny Eagle Road, Standish ME 040840 Originally built in the late 1700's this post and beam home was solidly built from hand hewn timbers upon a field stone granite foundation. Beginning 1800's a second cape style home was added on to the original colonial house, expanding it into a very...
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    Standish, Maine 04084
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 24
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    Falmouth
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Central Heating
    • Washer
    • Balcony
    • Terrace
    • Ocean Views
    • Sauna
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Large, spacious, home on National Register allows plenty of room for guests to socialize inside and out. Walking distance to Portland Yacht Club, Handy Boat launch, town dock facility, walking trails, town beach, Town Landing Market, and Dockside Restaurant. Short drive to Freeport shopping and...
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    Falmouth, Maine 04105
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    Falmouth
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Wi-Fi
    • Satellite TV
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Adorable, quaint and ideally located Maine Beach cottage. Fully furnished with updated furniture, comfortable beds, and all the necessary amenities. Steps from private beach - bring your kayak, paddleboard or other water craft or just relax and watch the sailboats on the Bay and go fishing from the...
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    Falmouth, Maine 04105
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    Beautiful Cottage on Crystal Lake1 / 23
    (4)Excellent
    Gray
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Amenities & Details
    • Internet Access
    • Satellite TV
    • Central Heating
    • Grill
    • Waterfront
    • Porch
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 February 2017
    This cottage was clean and comfortable with beautiful views. The owners were very accommodating and helpful in suggesting family friendly activities in the area. With Pineland...
    Reviewed 4 September 2016
    Western exposure,with plenty of sun to enjoy crystal lake! A fully equipped home with everything you could need. Two kayaks are available to see the resident eagles and loons...
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    About this property
    Quiet retreat with western exposure on crystal clear lake. Furnished in a comfortable rustic style. Bedrooms have queen bed, full bed and bunk over a futon. The living room showcases a wall of glass overlooking the lake. Ambiance completed by a propane stove on opposing wall. Newly remodeled...
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    Gray, Maine 04039
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 7
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    Waterfront Fun Pet Friendly Vacation Rental Camp1 / 23
    (7)Very good
    Gorham
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Terrace
    • Porch
    • Patio
    • Parking
    • Balcony
    • Grill
    • Central Heating
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 August 2016
    Great rental. Very relaxing and quiet. Really clean and fully stocked with everything you would need. Just bring yourself and food. We loved it here and was sad when vacation...
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    About this property
    Waterfront camp in Maine for weekly rent that offers peace, relaxation and fun for a family or small group. The camp is located on the Presumpscot River in Gorham, Maine. So unique and offers up 5 to sleep comfortably in any of the 2 bedrooms and an L-shaped couch in the living room. A...
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    Location Information
    Gorham, Maine 04038
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 5
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