Home Vacation Rentals By Owner In Windham, ME

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Exceptional(17)

$716.14

/ Nightly
Cottage

Little Sebago Lake - Private Sandbar With A White Sand Beach - Full Sun

Windham, Maine, United States

Grandview Point offers you an opportunity to enjoy a traditional Maine Lake experience in an updated summer cottage established in 1924. The Lake offers 9 miles of pristine water protected by the Little Sebago Lake Association for water, sand, vegetation, fish, and wildlife quality. There are three basins that make up the miles of water to explore, the middle basin of the lake has a public boat ramp where you can launch your boat and moor it on Grandview Point’s dock. Near the cottages dock there is a canoe and a rowboat with life preservers for your use; each person is required to wear a preserver in the State of Maine. The cottage is surrounded by three sides of water with a private sandy-bottomed beach in a cove and has a gradual entry that is safe for swimming. From the beach you have a view of “The Narrows” which enters back into the middle basin. The lake is stocked with brown/rainbow trout and bass by Maine’s Inland Fisheries. Five-pound bass have been caught off Grandview’s dock, just a note: A Maine fishing license is required for each person. A permit can be purchased from the Town of Windham or at the local Walmart that is 2-3 miles from cottage. The beach has full-sun all day with some birch trees if you prefer shade, there under the birch trees you will find four lounge chairs that can be moved about. On the beach closer to the cottage is a gas fire pit with four adirondack chairs; we supply one full tank of propane for your visit. There is also a gas grill with one full tank of propane.brbr Grandview Point is a two story summer cottage, the first floor has a fully stocked kitchen: refrigerator, stove/oven, microwave, toaster, blender, coffee pot, Keurig, pans, lobster pots, grilling utensils, dish soap, dish/hand towels, cleaning supplies, a dining room, and a living room with fireplace. Off the living room is a porch with an eight-foot picnic table that looks out onto the beach and lake; this is where everyone gathers for meals. The second floor has four bedrooms with the bathroom. There are two rooms that have king-size iron beds, and two rooms with queen-size iron beds. The beds have allergy covers on the mattresses and pillows, a mattress pad, and sheets with a comforter. The bathroom has a hand towel, soap, and cleaning supplies, you will need to supply bath/beach towels. Each of the rooms is finished with pine board floors, walls, and pine board ceilings with a ceiling fan. There are antique bureaus and decor that keeps with the original charm of the cottage. brbr Grandview Point is also conveniently located in the town of Windham. You will find that a 2-3 mile drive will bring you onto route 302 where there are super markets, restaurants, laundry, movie theater, amusement park with miniature golf, and an 9-hole golf course on Frye Island, Sebago Lake. A 10 mile drive will bring you to the town of Gray that has a wildlife sanctuary, 18-hole golf at Spring Meadow Golf Course, and access to route 95 that can bring you further north or south. A 20 mile drive east will bring you to Freeport with shopping at LL Bean and outlets, Wolfe’s Neck Woods State Park, and the Desert of Maine, and a 25 mile drive east will bring you to the city of Portland with it’s ocean views, wooden wharves, traditional lobster/clambakes, fine dining, shopping in the Old Port historic area, and many cultural events. brWhen making a reservation the payment should be made by e-check.
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Bath 1

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Sleep 8

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$552.01

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Cabin

Lakeside Cabin With Private Sandy Beach

Windham, Maine, United States

Directly on Little Sebago – Unusual Combination of Privacy and Convenience brbrRecently renovated 1920s craftsman-style Maine cabin combining rustic charm with modern convenience. Located directly on the lake, with spectacular, unobstructed water views. Private sandy beach with dock. Two kayaks.brbrPLEASE NOTE THAT OUR CABIN IS NOT APPROPRIATE FOR CHILDREN UNDER 5 YEARS OLD. We cannot accommodate pets.brbrThe space:brThe cabin has a totally unique location in a private family compound set on a beautiful wooded peninsula. Enjoy all day sunlight with water views both to the east and the west. Lounge in style on your own private sandy beach. Enjoy warm summer swimming and excellent fishing right outside your door. brbrThe house has a deck and 2 porches, one of which is enclosed. Great light. Great breezes. Beautiful views from every room, and lots of windows and glass doors to enjoy them from. brbrFast Internet. Internet TV. Dishwasher. Electric baseboard heat. Stone-built gas fireplace. Efficient “U” shaped kitchen with gas stove and new Bosch dishwasher. One full bath + ½ bath upstairs + an outdoor shower with a ramp directly to the beach. Gas grill. Games for a rainy day.brbr4 bedrooms: 3 with full beds, 1 with 2 twins. All beds are new, very firm, with soft mattress covers on top to give softness. Cotton sheets. Down pillows. Full-size casement window in each bedroom. Comfortably sleeps 5.brbrFantastic location! 2 hours from Boston. 30 minutes from Portland. 7 minute drive to Windham shopping, restaurants, and entertainment.brbrLittle Sebago has 5.5 miles of lake to explore and enjoy. There are three bays, each with its own personality, with lots of different features. brbrShared washer and dryer in the garage are yours exclusively to use every day after 2pm.brbrPlease keep in mind that this is a lakeside cabin in the Maine woods, with all inherent plusses and minuses. You will, for example, encounter mosquitos and other insects, although only rarely during the day. Our cabin is a beautiful, unique, wonderful place, but it is not The Hamptons.brbrPLEASE NOTE THAT OUR CABIN IS NOT APPROPRIATE FOR CHILDREN UNDER 5 YEARS OLD. We cannot accommodate pets.brbrGuest Access:brGuests have exclusive access to all parts of the cabin, the private beach, and the dock. Guests are welcome to access the front portion of the garage for trash disposal, laundry, kayak paddles and life vests. We live next door, and our canoe is available anytime. Paddles and additional life vests too.
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Bath 2

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Sleep 5

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$974.46

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Private Vacation Home

Sunny Waterfront Family Friendly Little Sebago Home

Windham, Maine, United States

***September 2024 update***brThere are only 4 nights available for the remainder of 2024: September 3rd to 7th. This is the week right after Labor Day, when the lake is quiet and the weather is generally awesome. We've lowered the nightly price for a short stay of 3-4 days instead of a full week. Contact us if you have questions or are interested in these days.brbrCamp Cal-a-Mac-ki is a 5 bedroom, 3.5 bath private home situated on .75 waterfront acres. brbrShared spaces:brThe great room features couches and chairs around a wood burning stove and cathedral ceilings with amazing lake views through floor-to-ceiling windows. Two sets of French doors open onto the deck, which provides comfortable seating for sharing a drink or tucking into a book while keeping an eye on the action down at the lake. The deck also features a large dining set for al fresco eating as well as a grill. brbrThe kitchen is stocked with everything you'll need to feed a crowd, and the 10' dining table just adjacent is perfect for shared meals inside.brbrThe basement television room is equipped with a 65 TV and pullout queen sectional sofa, as well as an air hockey table. There are also many board games and puzzles for both kids and adults which can be played here or on the second floor game table.brFinally, at the waterfront you'll find plenty of chairs to sit on the beach and a seasonal dock to tie up your boat (bring your own or rent one nearby). There's also a swim platform offshore, as well as a canoe, kayaks, and a paddle board to use.brbrBedrooms and bathrooms:brThe primary bedroom is located on the first floor. It features a queen mattress, a full bath, large closet, and a television. There are ceiling and portable fans for warm nights.brThe second floor contains queen and king bedrooms, as well as a bunk room that sleeps eight kids in grand camp style (4 twin beds with two twin trundles). Each room has ceiling and portable fans. There's a full bathroom on this level as well.brbrIn the basement you'll find a king bedroom, a queen pullout sofa in the television room for overflow sleepers, and another bathroom with a shower. brbrEach bedroom and bathroom is stocked with quality bed linens and towels.brbrLocation:brLittle Sebago Lake is the smaller sister of Big Sebago. The lake is just over 2000 acres and is divided into three basins, each connected by a narrow. Our house is located on the lower basin, where there is great fishing to be had around several small islands. The house is less than 10 minutes from major shopping in Windham, 10 minutes to I-95, and 30 minutes to Portland. brbrWe've rented vacation homes on three continents. Come see why we chose to settle on Little Sebago Lake, and enjoy the comfort we've put together at Camp Cal-a-Mac-ki.
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Bath 4

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Sleep 16

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$468.7

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Private Vacation Home

Little Sebago Lake Retreat with Sand Beach on a Private Point

Windham, Maine, United States

Relax and unwind at the Little Sebago Teahouse lakeside retreat with lake views from every room. A sand beach framed by pine trees, sand-bottom swimming area with a dock and raft to enjoy, and your own sandbar for water play or sand castles on beautiful Little Sebago Lake - over 400 feet of shoreline on a private half acre wooded point with an outdoor ping pong table and a sunny clearing for croquet, badminton, horseshoes, and other games. br. brThe Teahouse is designed in the style of a Japanese teahouse, featuring an open plan designed to adapt traditional Japanese rural architecture to a wooded lakefront setting with glass sliders, skylights and porches to embrace the natural world. A history of the Teahouse and many more photos of the lake and home can be found on our website LittleSebagoTeahouse. brbrThe main level is dominated by a great room, a high ceilinged, timbered space, that encompasses the living room, with its fireplace, a dining area, a fully-equipped kitchen, large screened porch with gas grill., and wrap-round deck.brbrOn the second floor balcony, shojii screens set off the master bedroom suite with a king-size bed, and European-style bathroom. A window in the tiled shower and the private balcony overlook a pine grove. The guest bedroom sits on the first floor, a tatami-floored space with its own private entrance, and sleeps two adults or two children. It is set off from its adjoining bathroom (also with shower) by more sliding screens. brbrThere is also a special sleeping loft with two futons and its own circular staircase that looks down over the living room, perfect for kids. brbrRelax on the wrap around deck or have dinner on the screened porch. With amenities like WiFi, a washer/dryer, dishwasher, smart tv and AC, your stay will be enjoyable and stress-free.brbrYou're sure to make fantastic memories with a stay at our place.
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Sleep 6

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Exceptional(1)

$362.17

/ Nightly
Cabin

Private Hilltop Cabin, Lakes and Trails Abound

Windham, Maine, United States

The ideal getaway in the heart of Sebago Lakes Region. One of a kind, end of a private road, no traffic here. Sleeps 8 comfortably (2 queens, 4twins) with a living area large enough, too. Feels like your in the wilderness yet only 2mi to town or 20mi to Portland.brThe spacebrVery Private, Open concept with catwalk to loft, sunrise and sunset covered porches. Play some crochet, volleyball or frisbee in the yard. Pour a glass of wine, light a fire in the Russian fireplace, chiminea or fire pit. Relax in the claw-foot tub or play the organ in the living area. Gas cook-top and oven to cook up a gourmet meal. Two closed door bedrooms and one open loft.brbrEnjoy the seclusion, the only neighbors visible from the property are the trees, turkeys or deer, and I saw some rabbit tracks the other day. But, definitely not isolated only 2 mi to an abundance of shopping/restaurant options or 20 mi to so much more in Portland.brGuest accessbrFishing on Trout Stocked Little Sebago Lake is within walking distance. Big Sebago Lake State Park is a 12 mi drive or bike trip. Backdoor to hiking Snowmobile/mountain bike trails. 5 min to town, 30 minutes from Portland, 30 miles to the coast and just 2 1/2 hrs from Boston.brEnjoy the seclusion, the only neighbors visible from the property are the trees, turkeys or deer, and I saw some rabbit tracks the other day. But, definitely not isolated only 10 minutes to an abundance of shopping/restaurant options.brThere is one Kayak at the property, you will need to provide your own flotation device. W/D are available to weekly+ guests only.brOther things to notebrThis property is right in the middle of the coast and the mountain ranges which makes it possible for all kinds of 1/2 to full day trip options. The 2 + miles in from 302 are not paved. In colder (snowy) weather 4 wheel drive is a must, there is a small hill to get in to the cabin.
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Bath 2

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Sleep 8

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Exceptional(1)

$358.43

/ Nightly
Cabin

Classic Maine Cabin, Private Waterfront Easy Access to Nearby Amenities

Windham, Maine, United States

Take a step back in time and a step forward towards relaxation. Consider this cabin your home away from home while you visit Windham This camp Is on Pettingill Pond in Windham Maine. It has water views, boating, fishing, indoor/outdoor fireplaces, and amazing proximity to amenities for those seeking creature comforts. It has heat and air conditioning to keep you comfortable in hot or cold weather.brIncluded with your stay are three stand-up paddle boards, two fishing rods and fishing accessories, a canoe, and a Kayak. Life jackets and paddles are also provided.brThe spacebrFor those looking for a hotel-type of experience, this is not it! :) It smells like a Maine camp and looks like a camp inside, and out. To me, though, that’s where it shines. You can get a hotel room, just about anywhere, but this Maine camp is just the right place to make memories that can last a lifetime. And if for some reason you want a little bit of civilization after spending some time on the beautiful, quiet, and peaceful Pettingill Pond, you can ride a bike or drive to a large number of attractions just minutes away. Your options for off-pond activities include an Amusement park (Seacoast Adventure), a movie theater where you can eat dinner while enjoying the movie (Smitty’s), a classic drive-in movie theater (Prides Corner), Starbucks, Walmart, Chipotle, and too many other shops and restaurants to list here. For those with Electric vehicles who need EV charging (Tesla, Rivian, Ford, Nissan, etc) - electric charging stations are 3 minutes away (Supercharger and ChargePoint).brbrSo book your stay today and make some wonderful Maine Memories.brbrThings that guests should know:br1) There is a bedroom in the smaller building separate from the main house (the “bunk house). It is a separate structure that’s about 10-15 steps from the main house. The main house has a pull-out couch with a memory foam mattress and an air mattress is available. The main house is the second bedroom. There are no doors in between rooms in the main house (the bathroom does have its own door.)br2) While there is a tub in the bathroom in the main house, the only water heater in the main house is not large enough to make use of the tub.br3) The water heaters on the property are small and intended for quick showers. You won’t be able to take a long, hot shower in there.br4) There is a laundromat (Pratt Abbot) less than 4 minutes away that takes credit / debit cards and cash and can be used via mobile app. There is no washer / dryer on site, but there is a laundromat less than a mile away.brGuest accessbrGuests may access the main house, the dock area, and the bunkhouse at their convenience.brOther things to notebrThings that guests should know:br1) There is a bedroom in the smaller building separate from the main house (the “bunk house). It is a separate structure that’s about 10-15 steps from the main house. The main house has a pull-out couch with a memory foam mattress and an air mattress available. The main house is the second bedroom. There are no doors in between rooms in the main house (the bathroom does have its own door.)br2) While there is a tub in the bathroom in the main house, the only water heater in the main house is not large enough to make use of the tub.br3) The water heaters on the property are small and intended for quick showers. You won’t be able to take a long, hot shower in there.br4) There is a laundromat (Pratt Abbot) less than 5 minutes away that takes credit / debit cards and cash and can be used via mobile app. There is no washer / dryer on site.br You'll have access to WiFi, a hair dryer, AC, an iron, coin laundry, and heating. Kickback, relax, and enjoy everything Windham and our cabin has to offer.br
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Bath 2

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Sleep 6

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$411.32

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Private Vacation Home

Windham Wind Down-Dock, Kayaks, SUPs, Fishing Rods

Windham, Maine, United States

☀ 15 Min Seacoast Adventure Parkbr ☀ 20 Min to Portland, MEbr ☀ 20 Min to Maine Wildlife Parkbr ☀ 25 Min to Portland’s Old Portbr☀ 25 Min to Portland International Jetportbr☀ 40 Min to Portland Head Lightbrbr→ Sleeps 6. 3 Bedrooms. 1 King. 1 Queen. 4 twin bunk bedsbr→ 2 Full Bathrooms with Shower/Tub Combobr→ Private Dock (mid-May to mid-October)br→ Modern, Well-Equipped Kitchenbr→ WiFi with 2 Smart TV’s & Streaming Servicesbr→ Fire Pit with Adirondack Chairsbr→ Kayaks, Paddle boards & Fishing Rods Providedbr→ Life Vests Available for Adults & Childrenbr→ Private Deck with Outdoor Seating & Grillbr→ Board Games and Booksbr→ Beautiful Lake Viewsbrbr☆☆ BEDROOMS ☆☆brbrThis gorgeous retreat accommodates 6 guests in 3 bedrooms all located on the 2nd level. The primary bedroom is fitted with a king-size bed and beautiful lake views. The 2nd bedroom, also boasting amazing lake views, is outfitted with a queen bed and all the comforts of home. The 3rd bedroom is perfect for kids or friends as it sleeps 4 in 4 bunk beds. All rooms offer plush bedding, air conditioning in the summer months, and ample storage to make your stay as comfortable as possible.brbr☆☆ BATHROOMS ☆☆brbrThere are two full bathrooms, each of them stocked with all the essentials you need for the duration of your stay.brbrThe 1st floor hosts a full bathroom with a shower-tub combination. It is located just off of the main living area near the kitchen and is easily accessible for all guests on the 1st floor.. The full bathroom on the 2nd level boasts a combination shower and tub. Worry about nothing with these thoughtfully stocked bathrooms that provide everything you need and more.brbr☆☆ KITCHEN & LIVING AREA ☆☆brbrThe bright and airy kitchen is fully equipped with all the appliances, utensils and cookware you need to feel at home. This thoughtfully-designed home provides an eat-In kitchen option with the dining seating 6 guests at the gorgeous wooden table.brbrThe first living area is situated on the main level of the home and is kitted with an HDTV with a Roku entertainment system and XBox, allowing full access to your favorite streaming services. Not interested in TV The living area hosts a comfy seating area where you can enjoy your favorite book or watch out the window as guests enjoy the lake. brbr☆☆ OUTSIDE SPACE ☆☆brbrThe exterior area of this home boasts gorgeous views and ample privacy. The front deck overlooks HIghland Lake, allowing you to appreciate the breathtaking views from this exclusive retreat while you prepare a meal on the BBQ. The back deck leads guests directly to the cozy fire pit for all to enjoy. Enjoy your days on the lake with complimentary access to kayaks and paddle boards. Bringing your boat Access to Windham Wind Down’s private dock is an amenity that is hard to beat! brbr★☆ Book Today & Let Us Take Care Of You In Windham! ☆★
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Bath 2

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Sleep 6

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$687.83

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Private Vacation Home

Hummingbird Hollow: 4BR, Lakeside, Private Beach

Windham, Maine, United States

Welcome to Hummingbird Hollow, a charming 4BR, 1.5-bath lakeside retreat in Windham, Maine. Enjoy a private beach for year round activities like boating, swimming, or ice fishing! The cozy home features a fully equipped kitchen, spacious living areas, and comfortable bedrooms, perfect for larger families. Just a short drive from local dining and attractions, this peaceful getaway offers the ideal blend of nature and convenience. Unwind and make lasting memories at this serene lakeside escape!brbrHere’s what makes Hummingbird Hollow so special:brbrBreakfast Nook with a View: Start your mornings off right in the breakfast nook, where you can sip your coffee while taking in peaceful lake views. It's the perfect spot to plan your day, whether you're heading out for a snow adventure or enjoying the tranquility of the lake.brbrLake Access: You'll have easy access to the lake year-round. In winter, it's great for ice fishing or just taking in the scenic views, and in summer, you can enjoy kayaking, fishing, or relaxing by the water.brbrPicnic Table by the Lake: Right outside, you'll find a picnic table perfect for enjoying meals by the water. Whether it's a sunny summer afternoon or a snowy winter day with hot cocoa, the lakefront setting is peaceful and beautiful year-roundbrbrKing Bedrooms: Sleep like royalty in one of our two King bedrooms, with stunning lake views just outside your window.brbrQueen Bedroom: This room features a comfortable Queen bed, perfect for a peaceful night’s rest.brbrBunk Room Fun: The Bunk Room has 3 twin beds, with the bottom one pulling out like a drawer for extra comfort! The top bunk is best for older kids or adults, as it may not be safe for very young children.brbrNeed more space A full height Queen sized air mattress is available for use, with the same high quality linens as on the traditional beds. It is all located in the closet under the stairs on the main floor (across from the 1/2 bath).brbrSnow & Lake Activities: From carving fresh powder on downhill or cross-country skis to snowshoeing, ice fishing, and snowmobiling in the winter, Hummingbird Hollow puts you at the heart of outdoor excitement. When the seasons change, enjoy fishing, kayaking, golfing, and swimming, all just steps from the lake. No matter the time of year, adventure is always within reach!brbrAt Hummingbird Hollow, you’ll experience the perfect blend of adventure and relaxation. Whether you’re here for winter thrills or lake-side serenity, this home is your ideal getaway. We can’t wait to welcome you and help you create lasting memories!brbrBook your stay today and let the adventure begin at Hummingbird Hollow!
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Bath 2

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Sleep 11

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$443.61

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Private Vacation Home

Cozy four-season getaway on Pettingill Pond

Windham, Maine, United States

Discover this fabulous 3-bedroom gem on Pettingill Pond in Windham. brbrThis charming house boasts 2 queen beds, 1 king bed, a set bunk beds and 1 twin bed, perfect for families and groups of friends alike. Enjoy waterfront access and beautiful views overlooking the pond from almost anywhere in the house. With amenities like a washer & dryer, well-stocked kitchen, WiFi, and AC, come relax and unwind effortlessly any time of the year.brbrThe open-concept living area features an eat-in kitchen, comfy sectional sofa and dining area. The house has two full bathrooms including a bathtub. The downstairs game room includes a pool table and dart board for extra fun. During the summer months, we also have a hot tub, dock and kayaks available for use. Pets are always welcome.brbrThe house offers close proximity to shopping and amenities in North Windham, only a 5-minute drive away. Seacoast Adventure Park is right across the street (however, it is a very busy road so please be careful if walking!) and provides year-round fun for all ages, with go karting and mini golf during the summer and snow tubing during the winter. The Deckhouse Tavern is part of the park as well and has great food and drinks. We are 40 minutes from skiing at Shawnee Peak and 40 minutes from everything Portland has to offer.brbrMake your getaway to Maine one for the books with a stay at our place.
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Bath 2

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Sleep 12

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