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Holiday Rentals in Gray

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    Beautiful Cottage on Crystal Lake1 / 23
    (14)Excellent
    Gray
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    The following rentals are within 15 kilometers of Gray.
    Windham
    5 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Raymond
    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Windham
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • DVD Player
    • Air Conditioning
    • Patio
    • Grill
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    Pet friendly
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    Smoking allowed
    About this property
    Hackett Road Hangout 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,...
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    Windham, Maine 04062
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    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
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    Windham
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
    • Cable/satellite TV
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    • Washer
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lady Pepperell 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...
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    Windham, Maine 04062
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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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
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    South Casco
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Washer
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    Pet friendly
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    Smoking allowed
    About this property
    Point Sebago Destiny Treat your loved ones to a classic Maine experience when you retreat to this darling cottage at Point Sebago, one of the most widely recognized family outdoor resorts in New England! You'll enjoy a private deck and firepit on pristine summer evenings, nights of board games and...
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    South Casco, Maine 04015
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Multi-Family Vacations-Anniversaries-Reunions. 8 Spacious Bedrooms1 / 29
    (8)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 yesterday
    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 24 September 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
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    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
    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
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    Yarmouth
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Washer
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    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Three bedroom home that can accommodate 8 guests, water access from the dock, outdoor fire pit, high end finishes.. A Cousins Island home which has kept it’s historically significant past yet has been tastefully updated using local architects and the owners long time builder based out of...
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    Yarmouth, Maine 04096
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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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
    • 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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    Location Information
    Windham, Maine 04062
    Holiday Rental House - 3 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
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    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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    South Casco, Maine 04015
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Secluded & Serene location. Just perfect for your Family to reconnect.1 / 29
    (5)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 1 week ago
    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...
    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...
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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
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    Windham
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Wi-Fi
    • Grill
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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
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    Windham
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    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
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    Danville
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    The Tentrr Hill Top Camp at Valley View Farm offers peace and quiet, lovely views of fields with all the privacy that your heart desires. Hiking and biking trails abound around a working farm that is situated among 2,000 acres of protected land. Hill Top Camp sits on a high ridge that looks over...
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    Danville, Maine 04210
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Windham
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    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
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    Pownal
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Tentrr Your Own Private Meadow you have your very own private meadow campsite and Royal River frontage for fishing. Over 17,000 brook trout were stocked in the Royal River in 2018. Very secluded site yet close to many activities. Visit the last remaining active Shaker village in the world on...
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    Pownal, Maine 04260
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Windham
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Parking
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    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
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    Yarmouth
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly renovated fully-furnished 1,000 square-foot apartment with new wood floors and dishwasher, all-utilities included, washer and dryer in building, off-street parking, in owner-occupied two-family home, walking distance to bakery, restaurants, grocer, riverfront walking trail, harbor. Quiet...
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    Yarmouth, Maine 04096
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Windham
    3 Bedrooms, 1 Bathroom, Sleeps 9 Quick View
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    • Wi-Fi
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    • Skiing: Property Is In A Ski Resort
    • Waterfront
    • DVD Player
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    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
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    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
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