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Windham Vacation Rentals

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    All 19 Rentals in Windham
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    Windham
    5 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Windham
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Windham
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Windham
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Waterfront
    • Patio
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Wi-Fi
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Serenity on Little Duck Pond You'll be just 30 feet from the serene shores of Little Duck Pond when you escape to this lakefront home in Windham, where you'll be treated to 262 feet of waterfront, a sandy entry area, and a private dock where you can sit and soak in the summer sun. Begin each...
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    Windham, Maine 04062
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Windham
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Washer
    • Wi-Fi
    • Balcony
    • DVD Player
    • 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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    Windham, Maine 04062
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Windham
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Tentrr Tranquil Hide Away campsite is a secluded campsite in the middle of twenty wooded acres in Windham, Maine. You can drive right up to your site, conveniently located twenty minutes from Portland, Maine and ten minutes from Big Sebago Lake. The site also offers close-by access to Little...
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    Windham, Maine 04062
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Windham
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Wi-Fi
    • Grill
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Hillside Cottage is a cottage at Sebago Lake Lodge and Cottages. On the first floor you will find two bedrooms (with full size beds), dinning area, 1/2 bath and kitchen. Escape down the spiral stairs to the master suite with two sofas (one is a pullout sofa) wall mounted tv, electric fireplace, and...
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    Windham, Maine 04084
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Windham
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
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    Pet friendly
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    About this property
    Lakeside Cottage just added to the rental market. Refinished and ready for you to enjoy the summer. 1 bedroom, loft area, and sleeper sofa for sleeping arrangements. Boat dock, fishing, swimming, enjoying the lake and nearby Portland are just a taste of what this getaway will provide. Have the...
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    Windham, Maine 04062
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Windham
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy spectacular views night and day, beautiful sunsets, fires on the seculled beach, clear fresh water swimming all within 7 minutes to the convenience of Windham's stores and many restaurants. This very spacious, centrally heated three bedroom house is directly on the lake with a sandy pebbled...
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    Windham, Maine 04062
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Windham
    3 Bedrooms, 1 Bathroom, Sleeps 9 Quick View
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    • Wi-Fi
    • Washer
    • Skiing: Property Is In A Ski Resort
    • Waterfront
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Find 'home' on Sebago Lake's shore at this well-loved 3-bed, 1-bath Raymond vacation rental. The cottage provides instant access to your favorite lake activities thanks to its private dock and sandy beach. After a day of boating, feast al fresco at the picnic table followed by s'mores around the...
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    Windham, Maine 04071
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 9
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    Windham
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Internet Access
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Second floor Condo featuring one bedroom, one bath and an open kitchen - living room combination. Patio doors open onto your deck that is equipped with a gas grill. Shared swimming area with a gas fire pit. Beautiful sunsets overlooking the White Mountains Very private feeling yet only 4 miles to...
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    Windham, Maine 04062
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    The following rentals are within 10 kilometres of Windham.
    Raymond
    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • DVD Player
    • Patio
    • Wi-Fi
    • Grill
    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Little Sebago Landing 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...
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    Raymond, Maine 04039
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 7
    Raymond
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Air Conditioning
    • Private Garden
    • Wi-Fi
    • Waterfront
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cabin on the Water Cozy, rustic, and gorgeously situated on the western shores of Little Sebago Lake, this Windham cabin is perfect for a quiet lakefront getaway to the Maine countryside. Bring along your kayaks to launch from the private dock, take an afternoon nap in the hammock after a day out...
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    Raymond, Maine 04062
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Multi-Family Vacations-Anniversaries-Reunions. 8 Spacious Bedrooms1 / 29
    (9)Excellent
    Raymond
    8 Bedrooms, 5 Bathrooms, Sleeps 21 Quick View
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    Amenities & Details
    • DVD Player
    • Central Heating
    • Porch
    • Waterfront
    • Grill
    • Patio
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 21, 2019
    I can’t say enough about our family vacation at Kossow Lodge. You would think with a dozen of us, things would get crowded but this place is huge and had so many different...
    Reviewed September 24, 2018
    For the past 40 years 13 of us have been gathering for our yearly "Annual." In the past we have gone to Cape Cod and Martha's Vineyard. To celebrate our 40th year, we...
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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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    Raymond, Maine 04071
    Holiday Rental House - 8 Bedrooms, 5 Bathrooms, Sleeps 21
    Raymond Retreat Brand New Luxury Lake House on Panther Pond1 / 44
    (1)Excellent
    Raymond
    4 Bedrooms, 4 Bathrooms, Sleeps 14 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
    Reviewed 2 weeks ago
    Raymond Retreat has not missed one detail in making our vacation simply wonderful! They have everything from a perfectly outfitted kitchen to stacks of movies and games to...
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    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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    Raymond, Maine 04071
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
    Secluded & Serene location. Just perfect for your Family to reconnect.1 / 29
    (6)Excellent
    Raymond
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Amenities & Details
    • Parking
    • Porch
    • Grill
    • DVD Player
    • Waterfront
    • Patio
    • Cable/satellite TV
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 5, 2019
    Crescent Lake is the perfect vacation spot and Nancy and Derek are the best hosts. The place is quiet, relaxing and there are so many things to do between swimming, kayaking or...
    Reviewed August 13, 2019
    One of the best vacations I’ve had with the family. We look forward to visiting every year and hope to for years to come . Truly a vacation , yet it still feels like a home away...
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    About this property
    Check availability calendar. This property is a seasonal rental. Aframe is closed from mid October to early May Fishing is great year round. Our A-frame is secluded and just perfect for families to reconnect. Located on the waterfront of Crescent Lake,Raymond, Maine.This cottage has 2 BR plus...
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    Raymond, Maine 04071
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
    Raymond
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Plan your escape with family and friends to this 3-bedroom, 1-bath cottage in Raymond! Filled with rustic charm, this vacation rental is set up for your arrival and offers a well-equipped kitchen, direct lake access, a gas grill, and much more! Spend your days fishing off the lengthy dock, canoeing...
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    Raymond, Maine 04071
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Raymond
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Mountain Views
    • Ocean Views
    • Waterfront
    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Get out on the water with a stay at this 2-bedroom, 1-bathroom Raymond vacation rental cabin. Sitting on Panther Pond, this property features a 200 ft sandy beach complete with a dock, beach chairs and grill area. If you need more lake views, explore Sebago Lake State Park or cast a line in...
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    Raymond, Maine 04071
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Raymond
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
    • Wi-Fi
    • Mountain Views
    • Cable/satellite TV
    • Ocean Views
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sitting on Panther pond with a sandy beach and dock, this 2-bedroom, 1-bath Raymond vacation rental makes for a peaceful lake getaway. Spend sunny days reeling in a catch from the dock or explore other nearby waters like Sebago Lake or Raymond Pond. Take a hike through Tassel Top Park, catch a...
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    Location Information
    Raymond, Maine 04071
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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