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Holiday Homes in Windham

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    All 23 Rentals in Windham
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    Windham
    5 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Windham
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Windham
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Windham
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Washer
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    • Balcony
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    • Grill
    • Terrace
    • Cable/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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    04062, Windham, Maine
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Windham
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
    • Internet Access
    • Parking
    • Air Conditioning
    • Waterfront
    • Cable/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...
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    04062, Windham, Maine
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Windham
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Parking
    • Internet Access
    • Grill
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    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Reconnect with your friends, family, and loved ones at this charming Windham property, a comfortable and convenient summer escape with three separate cabins, a gorgeous deck that overlooks Sebago Lake Basin, and easy access to a neighborhood beach, moorings, and a boat launch on the lakeshore....
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    04062, Windham, Maine
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Windham
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Parking
    • Grill
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    • Washer
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Head to Windham for a thoroughly relaxing and fun getaway with this cozy, three-bedroom cottage featuring a deck, gas grill, and outdoor firepit, as well as easy access to town and the slopes. With the lake just a short walk away and Windham proper only eight miles away, you'll be set for the...
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    04062, Windham, Maine
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    Windham
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
    • Internet Access
    • Parking
    • Grill
    • Cable/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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    04062, Windham, Maine
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
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    The following rentals are within 15 kilometres of Windham.
    Enjoy September and October Days at Charming 4-bedroom on Beautiful Sebago Lake1 / 26
    (11)Very good
    Sebago
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Porch
    • DVD Player
    • Washer
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Cottage is charming - incredible location on Lake Sebago with wonderful water views and lapping wave sound track right outside the doors and windows. Boating, fishing, golf...
    Reviewed 16 September 2017
    Very Quite Relaxing what a view. Adele very pleasant and particular about making the cabin comfortable . The flowers on the tables a great touch . Fire by the water at night was...
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    About this property
    Morningside, at the water's edge, is a delightful, classic, well-maintained rustic cottage with every modern convenience. Its spacious living room has a large stone fireplace (wood is provided) and dining area. The fully-equipped eat-in kitchen includes a dishwasher and microwave. The screened...
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    04029, Sebago, Maine
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Sebago
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Ocean Views
    • Air Conditioning
    • Waterfront
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This very spacious, centrally heated three bedroom house is 60 feet from the lake with lawn opening onto a secluded sandy beach cove. In the summer months, the house is rented on a weekly basis. In the Fall, rentals are limited to 3 days or more. It is very private with vivid colors and spectacular...
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    04029, Sebago, Maine
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Sebago Breezin' Long Beach Sebago Lake Maine1 / 26
    (2)Excellent
    Sebago
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • DVD Player
    • Porch
    • Outdoor Dining Area
    • Cable/satellite TV
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 September 2015
    Very nice place to stay and Sid was a great host. We enjoyed our stay and the location was great for our day trips. Looking forward to our next visit.
    Reviewed 2 June 2015
    We thoroughly enjoyed our stay at Sebago Breezin'! The house is very comfortable with a fully equipped kitchen, screened in front porch and nice deck with a grill out back. The...
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    About this property
    Summer rentals are Check in Saturdays at 3 PM and check out is Saturday at 10:AM Please leave the Camp broom clean so that you are not charged an extra cleaning fee..Remember NO smoking and NO pets..Keep trash in the cans with lids on....Please respect the beach and keep your things picked...
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    04029, Sebago, Maine
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Sebago
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Wi-Fi
    • Grill
    • Washer
    • Parking
    • Waterfront
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious 4 bedroom shorefront cottage on Sebago Lake! Large, sunny kitchen and cozy living room. 2 full baths, entertainment room, washer and dryer. Beautiful views, sandy beach, private lakeside dock and boat mooring. Great fishing and boating. Short drive to hiking, biking and local general...
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    04029, Sebago, Maine
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    South Casco
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Washer
    • Central Heating
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ideal for entertaining 4-season getaway for friends or family! Freshly painted, well-maintained, 2 bedroom, 1.5 bathroom home is located within the 775 acre Point Sebago Resort. The master bedroom has a king sized bed, large closet and a full bathroom. The second bedroom has 2 - twin beds, closet...
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    04015, South Casco, Maine
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Standish
    6 Bedrooms, 4 Bathrooms, Sleeps 22 Quick View
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    • Washer
    • Porch
    • DVD Player
    • Secure Parking
    • Central Heating
    • Grill
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 unique and large country home. This combination...
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    04084, Standish, Maine
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 22
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    Raymond
    4 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Patio
    • Grill
    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Luxury lake house on tranquil Panther Pond available for year-round vacation rental. Enjoy swimming, kayaking, fishing, boating, and relaxing with friends and family on 2+ acres of secluded lake front property and more than 200 feet of pristine waterfront. Everything about this property is BRAND...
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    04071, Raymond, Maine
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 16
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    Beautiful Cottage on Crystal Lake1 / 23
    (9)Excellent
    Gray
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Waterfront
    • Porch
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    Great location on Crystal Lake~ nightly view of Sunsets and warm breeze made our stay even more enjoyable. Very comfortable for our family of 4 with two littles 6 yr and 1 yr...
    Reviewed 17 August 2017
    What can I say? The cottage is everything you could ask for and more. It was very clean and well kept. The lake was as its name, crystal clean. It was close to restaurants...
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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 is completed by a propane stove on opposing wall. Newly remodeled...
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    04039, Gray, Maine
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 7
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    Standish
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    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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    04084, Standish, Maine
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    20 PERCENT DISCOUNT all open time $240/nite & $1640 for full week.1 / 29
    (4)Excellent
    Raymond
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Parking
    • Porch
    • Grill
    • DVD Player
    • Waterfront
    • Patio
    • Cable/satellite TV
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 August 2017
    My family and I just returned from our first stay in One A-Frame of Mine and it was just perfect! The location is wonderful, quiet and relaxing but close to store, towns if...
    Reviewed 7 August 2017
    My parents brought my brother and me to the A-Frame as young kids for years beginning in 1980. It was the highlight of our summers and the magic is still here. I have been...
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    About this property
    20 PERCENT DISCOUNT now offered on open time remaining. 6/16/18--7/14/18 & 7/21/18--7/28/18 Also 8/25/18/18 -9/15/18. Now offered at $240 per night. OR $1680 FOR FULL WEEK Check availability calendar. This property is a seasonal rental. Aframe is closed from mid October to early May Fishing is...
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    04071, Raymond, Maine
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    BOOKING 2019 BIG SEBAGO LAKE  5 - STAR COTTAGE - SEE REVIEW STORIES1 / 54
    (3)Excellent
    Sebago
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • DVD Player
    • Waterfront
    • Internet Access
    • Cable/satellite TV
    • Air Conditioning
    • Mountain Views
    • Porch
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    RELAX IN PARADISE ON BIG SEBAGO LAKE - Fish, Boat, Swim, Day-trips, Dining-Out, plus much more. SPRING is a special time to visit Portland, coastal towns, and Big Sebago Lake. HIKE, BIKE, WALK, fish, tour, relax, boat, dine and explore the incredible beauty of the area. Here are some events that...
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    04071, Sebago, Maine
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Multi-Family Vacations-Anniversaries-Reunions. 8 Spacious Bedrooms1 / 29
    (3)Excellent
    Raymond
    8 Bedrooms, 5 Bathrooms, Sleeps 21 Quick View
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    • DVD Player
    • Central Heating
    • Grill
    • Waterfront
    • Patio
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 August 2017
    18 of us COMFORTABLY stayed at the spacious and immaculate Kossow Lodge the last week of July/August 2017. I was completely overwhelmed with the lodge's well kept grounds as we...
    Reviewed 2 August 2017
    My entire family has rented this house for 2 years in a row, and have had 2 excellent vacations. We will be returning next year as well. We have 9 adults and 11 children ages...
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    About this property
    Welcome to Kossow Lodge, Located on Crescent Lake in Raymond, Maine. Ideal for multi-family or large reunions, Kossow Lodge is a four-season, private home located on beautiful Crescent Lake, in the Sebago Lakes Region of Maine. With eight bedrooms and five bathrooms, Kossow Lodge comfortably...
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    04071, Raymond, Maine
    Holiday Rental House - 8 Bedrooms, 5 Bathrooms, Sleeps 21
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    Gray
    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come to Maine for a reprieve from life's busy pace and stay in this spacious, dog-friendly home in Gray, featuring easy access to two beaches at Little Sebago Lake and close proximity to town. Your lovable family dog is also welcome for a small nightly fee! Take the provided beach chairs to one of...
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    04039, Gray, Maine
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 7
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    Standish
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • DVD Player
    • Cable/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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    04084, Standish, Maine
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Standish
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Skiing: Property Is In A Ski Resort
    • Air Conditioning
    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ** Please note that the homeowner lives on site, in a completely separate unit, and may be present during your stay ** Enjoy a lake getaway to remember in this 1-bedroom, 1-bathroom vacation rental apartment in Standish. Located just 2 miles from Lake Sebago's top-notch water sports and gorgeous...
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    04084, Standish, Maine
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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