Vacation Rentals By Owner In Windham, ME

Cozy 1930's cottage nestled in a private cove 20 minutes from Portland and 40 minutes to Naples. The lake is fresh spring fed approximately 1X3 miles. Amenities include hot tub, 2 adult kayaks, 2 children’s kayaks, 2 paddle boards, gas grill, picnic table, hammock, and dock. Small beach area with fire pit. Internet is available, flat screen TV with DVD player and movie library. Bring your own towels and bedding. Also please observe the Windham Maine leash law.

Cottage

Lakefront Cottage with New HOT TUB. . Located only 20 minutes from Portland

Windham, Maine, United States

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Exceptional(38)

$689.79

This is an Upscale All-Season Vacation Property! This Highland Lake home is on two quiet acres with a small sandy beach, shallow entry to the lake (great for kids), 200+ ft shoreline, 50ft dock and all the amenities and activities to create memories for a lifetime. Sitting areas, dining, BBQ, hot tub, porch swing, fire pit, and hammock are all overlooking a beautiful 3 mile long lake within 5 miles of Portland, ME. A large yard offers pickleball, volleyball, bocce, croquet, wiffle ball, frisbee, lying in the sun and more. Enjoy the eagles, frogs, turtles, flowers, birds at the window feeder, fish, and more...just outside your door!brbrNew since 2022 is new kitchen appliances, quartz countertops in kitchen and bathrooms, queen bed upgrades, new pullout sofa and love seat with 3 new tables, new flooring in almost all rooms, added half bath, new pots/pans set, and more. Very well maintained.brbrThis is a home with all the comfortable living amenities as opposed to typical 'rentals' and thus you see the many 5 star reviews.brbrWhat to Expect: This wonderful lakefront home offers all you need for a relaxing lakeside vacation. Enjoy, swimming, kayaking, or just relaxing on the lawn, hammock, float or dock. The property comes furnished with 2 kayaks, 2 canoes, and plenty of life vests. An 8 person hot tub faces the lake. There is a great dock bench seat for morning coffee or watching the swimmers or wildlife, hammock for that afternoon snooze and fire pit for marshmallows and winding down in the evening. There is no off-season here! The hot tub is on year-round. In the fall you can enjoy some spectacular canoe/kayak rides and the plethora of hiking in the area. In the winter, you can ski Shawnee Peak which is just 45 minutes away or Sunday River which is 1.25 hrs away. Highland Lake offers wonderful ice fishing, skating, cross country skiing and beautiful snowmobile trails.brbrC'mon In! Step in the front door and immediately take in the breathtaking lake views you’ll find along the length of the house through large windows. The living room has several love seats, one that has 2 individual reclining, rocking seats and an HDTV and Bose CD/AM/FM Stereo. Two swivel and rocking (ahhh) chairs overlook the lake and are perfect for that morning cup of coffee watching the sun rise and the birds at the feeder or reading in the afternoon while viewing the kids jumping off the dock and swimming to the float, playing on the lawn, or laughing in Hot Tub just below. Perhaps a change of venue moving to the shade outside on the porch swing under the deck or to the hammock listening to the waves splash gently on the beach. Take an outdoor shower as you enjoy the sounds of nature and view of the beautiful lake.brbrThe dining table is large and there is an additional folding table to extend even further. The island has 4 stools for drinks and chatting while making a meal in the kitchen. There are two ACs for those hot summer days, a beautiful gas fireplace for those chilly winter nights, and everything in the kitchen from lobster cooking supplies to a pancake griddle to serving dishes and even owner spices, oils, and more to use at your convenience. Since this is a home while not rented, there will be all the extras needed that you won't find in a bare bones rental.brbrLake Information: Highland Lake is 3 miles long and up to 3/4 mile across with depths up to 65 ft deep. Highland Lake only offers a public hand carry boat launch for canoes and kayaks which keeps motor boating traffic low. Fisherman find small and large mouth bass, white and yellow perch, and pickerel. Other lake wildlife includes loons with their beautiful calls in the evening, eagles, ducks, blue heron, turtles, beaver, and more.brbrPortland, Maine has been named Best Restaurant City of the Year, Best City to Live, Safest City, and Best Craft Beer City in the World! Portland is only 5 miles away from the lake house!

Private Vacation Home

Private Lakefront Home-Hot Tub-Great for Families-Large Yard-Quiet-Shallow Entry

Windham, Maine, United States

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Select Dates for Price

Entire Modern Chic Home in Windham

Windham, Maine, United States

Kick back and relax in this calm, stylish space. Centrally located close to Sebago Lake, Portland’s Old Port, coastal Maine beaches, Skiing Mountains, Freeport & more! Enjoy this chic 2 bedroom home that is private yet minutes to all the excitement the Lake’s Region has to offer. You’ll enjoy everything this fully equipped home has to offer while being centrally located to all the best things in Maine! This cozy home is perfect for weekend stays or couples vacations! Guests have access to the whole 2 bedroom house. Each bedroom has a queen bed and closet. Towels and linens are provided. The kitchen is fully equipped with a coffee maker, blender & more!

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Exceptional(50)

$551.19

Highland PlayhousebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrIf you're looking for a peaceful, lakefront getaway where you can choose to either relax at home with your feet up or head out in a boat or kayak for exciting days on the water, tick off both boxes here at this absolutely charming, two-story lake house!brbrStep inside and discover a number of classic features combined with plenty of modern touches. Stock up your fridge and prepare your favorite recipes in the well-equipped, eat-in kitchen complete with stainless steel appliances, and then dine indoors at the kitchen table, in the formal dining area, or outside on your furnished deck. This home also includes a furnished sunroom, a cozy main living area with a TV for streaming your favorite channels, and a small room with a view off the primary bedroom upstairs - a wonderful spot for morning coffee or lazy afternoons with a good book and a mug of tea. Outside, cast a line from the dock or paddle off in one of the provided watercraft , You'll also find a gas grill for summertime barbecues and a lakeside firepit.brbrTHINGS TO KNOWbrFull kitchen (no dishwasher).brStreaming TV services require guest accounts to access.brTwo paddle boards and three kayaks are available for guest use, though guests are required to sign a waiver to use them.brbrIf you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. If you would like to add more dogs, please contact us.brbrParking notes: There is free parking available for 4 vehicles.brbrSecurity camera details: Outward facing Ring cameras around the home. These are not for guests use but will be up at the home. brbrPlease note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!brbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Cabin

Charming lakefront cottage with a dock, WiFi, & washer/dryer - dogs welcome

Windham, Maine, United States

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$514.01

Highland Lake is a beautiful private pristine lake located in Windham/Falmouth Maine. Our lake is fed by springs and streams. The south end of the lake empties into a channel and becomes a tributary of the Presumpscot River, and then onto Casco Bay. We have some of the best fishing and sunsets around! The lake is perfect for kayaking, viewing wildlife, swimming, sunning, relaxing with friends, family, books, puzzles and enjoying great local food! Youll find that Fayth Cottage is in a peaceful setting nestled in a classic lakeside community speckled with cottages and homes all along a preserved shoreline. You will have private access to 100 feet of shoreline, a stationary dock and a floating dock. Enjoy a beautiful sunset, listen to the loons or take our double and single kayaks out on the water to explore the lake. Feel like a change of pace Jump in your car and head to Portland and in 15 minutes you'll find yourself in a food lovers paradise! The city is home to some of the best chefs who have relocated from around the globe, making Portland one of the hottest spots nationally on the food scene. You can also hop on a ferry in the Old Port to visit or tour the islands in Casco Bay. There are museums, music venues, and historical sites (not to mention water) all in and around the greater Portland area. In addition to our beautiful spot on Highland Lake there are beaches close by for day or afternoon trips. Freeport, home of our beloved LL Bean flagship store and campus is only a car ride away. There you will find outlets, coffee shops, restaurants, ice cream parlors, cafes and much more. Also located in Freeport is Wolfes Neck Woods State Park. It's well worth checking out if you want to decompress from an afternoon of shopping. Its a short drive from the village and the views are breathtaking. The park is composed of woodlands, estuaries, rocky coast line, guided nature walks and osprey watching. One of the many amazing things about Highland Lake is its proximity to vastly different landscapes in the surrounding area. We have mountains, rivers, lakes, ocean, hiking, fishing, boating all within a reasonable distance to make your vacation filled with a rich experience of what our beautiful state has to offer. Whether you want to drop your bags and kick back for your entire stay at our home, or maybe you have an interest in exploring and experiencing the many things our area has to offer, you couldn't have picked a better spot than Fayth Cottage! By the end of your stay we hope that you will understand why we affectionally say Maine, the way life should be!

Cottage

Classic Maine waterfront cottage on pristine Highland Lake Windham/Falmouth

Windham, Maine, United States

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$1343.03