Vacation Rentals By Owner In Raymond, ME

This charming traditional Maine cottage, located in the Sebago Lake Region of Maine, features a bunk house and guest house, all situated on a large private lot in a tranquil setting. Enjoy stunning views of the lake and the sunset from the west-facing property. The Main House has banked frontage with 12-14 stairs to the dock, and a gradual entry with soft ball-sized rocks. The Guest House is surrounded by a naturally sloping wooded lot, accessible via 9 stairs to a slightly sloping ramp, followed by another 3 stairs leading to natural rock steps, which lead to a shallow, gradual, rocky lake bottom. Sebago Lake is a large lake with plenty of boating opportunities, including access to Brandy Pond and Long Lake through the Songo River, providing over 40 miles of boatable waterway. Both docks are available for loading and unloading only, accommodating up to a 20-foot boat. When not in use, boats must be kept on the moorings, which can accommodate boats up to 21 feet in length. The property is well-appointed, providing a back-to-nature environment while still being close to shopping and recreational activities. The open level lot has a large lawn around the Main House, surrounded by woods, perfect for relaxing and enjoying the beautiful scenery.brbr2026 Rates: $835/night PEAK season; $580/night LOW seasonbrbr* Sheets, pillowcases, beach towels, and bath towels not provided *brbrFor VRBO bookings, please select no when prompted to opt out of the damage protection and travel insurance, as these services are offered directly through Krainin Real Estate after booking.

Traditional Maine Cabin, Bunk House, and Guest House on Sebago Lake!

Raymond, Maine, United States

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Bath

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$395.99

Nestled in the Sebago Lake Region of Maine lies this tranquil and rustic oasis. After passing through a children's camp and following a long, rustic road through woods, you will emerge at the secluded cottage, high above the water, where distant mountain views open up across Sebago Lake. Enjoy breakfast on the screened porch or deck as sunrise catches the tops of maples, pines, and granite boulders at water's edge. To reach the water, you take the rocky path down to a waterside deck, for a swim off the rocks or to paddle along the wooded shoreline. Another choice is to take the 50 stairs down to the west-facing deck at water's edge. Youngsters who can swim will spend hours exploring the rocky shoreline. Folks who prefer taking in the views from the porch or decks will enjoy gorgeous sunsets. Much natural beauty and privacy in this simple, nicely renovated 125-year-old fishing cabin. Wooded and natural with no visible neighbors and some open space. Cottage sits high above the water with steep access down to rocky water's edge. South access has decks on the rocky shore with a short swim ladder, plus a protected area for kids swimming and kayak/canoe launch. Explore the vast lake in the provided kayak and canoe.brbr2026 Peak Rates: $300/night 1 wk; $290/night 2-3 wks; 280/night 4+ wksbrbr* Sheets, pillowcases, beach towels, and bath towels not provided *brbrFor VRBO bookings, please select no when prompted to opt out of the damage protection and travel insurance, as these services are offered directly through Krainin Real Estate after booking.

SUMMER SPECIAL Vintage cottage w/ beautiful mountain views across Sebago Lake

Raymond, Maine, United States

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Bath

Sleeps

$395.99

Experience pure relaxation at a cozy, yet spacious cottage on the tranquil waters of Thomas Pond in Raymond. With its serene ambiance and breathtaking sunset views, this cozy waterfront property offers you the Golden Pond feel. Thomas Pond is a haven for fishing, swimming, and wildlife viewing, covering approximately 442 acres. Take advantage of the rowboat, canoe, 2 kayaks, and two paddleboards to explore the calm pond. The brand new dock can accommodate up to a 12' boat, complete with a ladder for swimming and sunbathing. The property's level, grassy terrain is lovely, with a private and scenic view, and some brush and rocks along the shoreline. The cottages location is conveniently close to shopping, restaurants, recreational facilities, and cinemas for an all-encompassing experience.brbr2026 Rates: $358/night PEAK season; $300/night LOW seasonbrbr* Sheets, pillowcases, beach towels, and bath towels not provided *brbrFor VRBO bookings, please select no when prompted to opt out of the damage protection and travel insurance, as these services are offered directly through Krainin Real Estate after booking.

Cozy pet-friendly cottage on Thomas Pond with excellent sunset views!

Raymond, Maine, United States

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Bath

Sleeps

$413.6

Experience all the Sebago Lake Region has to offer at this spacious waterfront home on Raymond Pond. Bring your family and furry-friend along to enjoy the beautiful sunrise views each morning and create everlasting memories roasting s'mores around the campfire at night. The yard is mostly level, featuring a lawn area and natural ground cover leading down to the waterfront. The shoreline is rocky, with 6 steps leading to the dock and an additional 2 steps from the dock into the water. The dock can accommodate up to a 20' boat, and you'll also have access to 1 paddleboard and 2 kayaks (1 single and 1 double). The property is conveniently situated, with easy access to local activities, restaurants, and shopping. brbr2026 Rates: $358/night PEAK season $286/night LOW seasonbrbr- 1 dog max with $100.00 pet feebr- Window A/C unit in all upstairs bedroomsbrbr* Sheets, pillowcases, beach towels, and bath towels not provided *brbrFor VRBO bookings, please select no when prompted to opt out of the damage protection and travel insurance, as these services are offered directly through Krainin Real Estate after booking.

Pet-friendly home on peaceful Raymond Pond with beautiful sunrise views!

Raymond, Maine, United States

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Bath

Sleeps

$391.52

Escape to this classic Maine camp on Little Sebago Lake, the perfect getaway for families — and your furry friends! The property features a level front and back yard with grass stretching right to the water’s edge, leading to a tranquil cove with a sandy, gradual entry perfect for swimming and wading.brbrSpend your evenings around the fire pit, roasting s’mores and listening to the soothing sounds of loons and owls. For water adventures, enjoy the paddleboard to explore nearby coves and islands, or bring a boat — the dock accommodates vessels up to 25 feet.brbrWith nearly 1,900 acres of connected waterways, there’s endless room to fish, paddle, or simply explore the beauty of Little Sebago Lake. Whether relaxing on the shore, paddling across the water, or enjoying a cozy campfire, this lakeside retreat is the ultimate Maine escape.brbrbr2026 Rates: $342/night PEAK season $286/night LOW seasonbrbr- Dogs allowed with $100.00 pet fee per pet.brbr* Sheets, pillowcases, beach towels, and bath towels not provided *brbrFor VRBO bookings, please select no when prompted to opt out of the damage protection and travel insurance, as these services are offered directly through Krainin Real Estate after booking.

Pet-Friendly Maine Camp on Little Sebago Lake – Sandy Shore & Dock

Raymond, Maine, United States

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Bath

Sleeps

$358.39

This charming cottage is just steps from the calm waters of Panther Pond in Raymond, Maine, offering a peaceful retreat surrounded by woods. Rustic yet well maintained, it delivers a true Maine vacation experience, with stunning waterfront views and easy pond access only 26 feet from the doorstep. Start your mornings with coffee on the deck or dock as the sun rises over the water, spend the day paddling in the included canoe or kayaks, and end it listening to the loons echo across the lake — all in total privacy and tranquility. For outings beyond the pond, nearby Windham offers shopping, restaurants, and activities, making it easy to explore before returning to your serene lakeside escape.brbrInside, the cottage comfortably sleeps five guests, with space for two additional overnight guests for short stays. Fans and portable A/C units keep the space comfortable, while a fully equipped kitchen, washer (added 2026), WiFi, and TV provide modern conveniences. Outdoors, relax on the deck, enjoy meals at the picnic table, or take in the scenery from the dock. Dogs are welcome, making this the perfect spot for a family or small group seeking a true Maine lakeside escape.brbr- Dogs welcome ($100 per pet)br- Portable A/C units on main floor and upstairsbr- Dock accommodates a 10’ boat with mooring for a 16’ boatbr- Canoe and 2 kayaks includedbr- No outdoor fires permitted (fire pits, tiki torches, sparklers, etc.)br- Sheets, pillowcases, and towels not provided (linen service available)brbrFor VRBO bookings, please select no when prompted to opt out of the damage protection and travel insurance, as these services are offered directly through Krainin Real Estate after booking.

Private Lakefront Retreat on Panther Pond | Canoe, Kayaks & Dock

Raymond, Maine, United States

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$1080.81

This gorgeous contemporary home offers stunning views of Raymond Pond and plenty of space for family and friends. With 4 bedrooms and 3.5 bathrooms, the main-floor master suite features a spacious bedroom, full bathroom with a TV, and a private sitting room with a second TV — perfect for a quiet evening in.brbrEven on rainy days, there’s no shortage of activities: enjoy the home gym, library, office, or the full game room complete with ping pong, foosball, darts, and a piano. Step outside to beautifully landscaped grounds leading to the shallow, sandy swimming area off the dock, which can accommodate a 20’ boat. Two kayaks and four paddleboards are provided for exploring the 346-acre pond.brbrRelax lakeside in one of two hammocks, take in the views from the screened porch, or gather around the outdoor fire pits in the evening — including a propane pit and a traditional wood-burning pit on the patio. Additional amenities include an oversized garage with space for two cars.brbrJust a short drive from recreational activities, restaurants, and shops, this Raymond Pond retreat combines luxury, fun, and convenience for an unforgettable Maine getaway.brbrbr2026 Rates: $800/night PEAK & LOW season; $743/night OFF seasonbrbr* Sheets, pillowcases, beach towels, and bath towels not provided (optional linen service available) *brbrFor VRBO bookings, please select no when prompted to opt out of the damage protection and travel insurance, as these services are offered directly through Krainin Real Estate after booking.

Spacious Luxury Retreat on Raymond Pond | Game Room & Private Dock

Raymond, Maine, United States

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Bath

Sleeps

$324.54

Experience the beauty of Maine's Sebago Lake Region at this charming, light-filled waterfront cottage on Panther Pond. Enjoy stunning lake views from the cottage, patio, and dock, all while maintaining a sense of seclusion and privacy. Take in the breathtaking sunsets and listen to the loons as they lull you to sleep. The sloping yard features large slab stairs that lead to the patio and dock, and the property borders a wooded area. The rocky shore provides deep-water access via a ladder on the dock or steps. This friendly neighborhood location includes a sports court for basketball, badminton, and volleyball, while a canoe and 2 kayaks are provided for you to explore the 3-mile long pond. For more water adventures, the dock can accommodate boats up to 24 feet, and the mooring can hold boats up to 14 feet. Outdoor enthusiasts will enjoy hiking at nearby Rattlesnake Mountain, with shopping and dining options available nearby. There is no shortage of activities to enjoy at this prime location!brbr2026 Rates: $272/night PEAK season; $243/night LOW seasonbr- This property rents Friday - Fridaybrbr* Sheets, pillowcases, beach towels, and bath towels not provided *brbrFor VRBO bookings, please select no when prompted to opt out of the damage protection and travel insurance, as these services are offered directly through Krainin Real Estate after booking.

Bright and cozy waterfront home on Panther Pond with stunning lake views!

Raymond, Maine, United States

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Bath

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$532.67

This cozy waterfront cottage is situated in a serene neighborhood on Papoose Island, with stunning views of Sebago Lake and excellent swimming opportunities. The property comes equipped with a swim float, pedal boat, and 12' rowboat for your use. The dock is capable of holding a boat up to 24' long so you can explore the 40+ miles of boatable waterway on vast Sebago Lake along with Brandy Pond and Long Lake via the Songo River. The cottage is surrounded by natural landscaping and wooded areas, with a cement landing complete with a picnic table so you can dine with a view! The waterfront is accessible via a few stairs from the house, and the property has a slightly sloping yard. When water levels are normal to low, the sandy, gravely beach creates an ideal spot for swimming, with a rock jetty offering protection for the swimming area. Don't miss out on this one-of-a-kind property!brbr2026 Peak rate: $425/night 1 wk; $415/night 2-3 wks; $405/night 4+ wksbrbr* Sheets, pillowcases, beach towels, and bath towels not provided *brbr- Window A/C units in the living room and sun porchbrbrFor VRBO bookings, please select no when prompted to opt out of the damage protection and travel insurance, as these services are offered directly through Krainin Real Estate after booking.

Cozy cottage on Sebago Lake with amazing views and excellent swimming!

Raymond, Maine, United States

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Bath

Sleeps

$562.68

Experience the serenity of Panther Pond at this charming 2-bedroom camp, complete with a bunkhouse. The property boasts beautiful views of the pond with just a few stairs leading directly to the shallow, gradual entry to the water - perfect for a refreshing dip! The bunkhouse features a queen bed, a cozy lounge area for TV watching or gaming, and high-speed internet connected to both cottages. Enjoy outdoor cooking with the gas grill, and relax in the evenings around the fire pit. Explore the pond with the provided canoe and kayak, or bring up to a 20' boat to keep on the dock. The level lot is adorned with flowers and a stone walkway, providing the perfect sanctuary to unwind and recharge in a picturesque setting.brbr- This property rents Friday - Fridaybr- 2 dogs max with $100 pet rent per petbr- 1 window A/C unit in main house + 1 in bunk housebrbr* Sheets, pillowcases, beach towels, and bath towels not provided *brbrFor VRBO bookings, please select no when prompted to opt out of the damage protection and travel insurance, as these services are offered directly through Krainin Real Estate after booking.

Charming pet-friendly camp on peaceful Panther Pond!

Raymond, Maine, United States

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$794.14

3 Large Bedroom, 3 Bathroom, Sleeps 8+ on peaceful lake in the Sebago Lakes Regionbrbr1st floor has bedroom with Queen and bunk beds, bathroom with tub and shower, washer and dryer. Open kitchen with table and chairs for 8+, living area and both sun room and screened porch with picnic table.brbr2nd floor has Master bedroom with Queen bed and private bathroom and bedroom with queen and twin bed with private bathroom.br

Beautiful, Private Lakefront Home on Crescent Lake in Raymond, Maine

Raymond, Maine, United States

3

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3

Bath

9

Sleeps

$670.48

New for 2026! Enjoy this spacious 4-bedroom, 2-bathroom home just 75 feet from the shore of Little Sebago Lake. Fully equipped with modern comforts, it offers stunning lake views, an east-facing orientation for beautiful sunrises, and plenty of space for family and friends to gather.brbrThe private waterfront features a gradual sandy entry for wading and swimming, a dock for boats up to 25’, and a kayak to explore the lake’s coves and islands. Located in Raymond, you’ll be close to restaurants, shops, and outdoor adventures in the Sebago Lakes Region.brbrBring your family, friends, and pets to enjoy this perfect Maine lake escape!brbr- Friday - Friday rentalbr- Linens are provided br- 1 dog allowed with $100 pet feebr- A/C units in the upstairs bedroomsbrbrFor VRBO bookings, please select no when prompted to opt out of the damage protection and travel insurance, as these services are offered directly through Krainin Real Estate after booking.

Little Sebago Getaway: 4 BR, 2 BA House in Raymond, Sleeps 9

Raymond, Maine, United States

5

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2

Bath

9

Sleeps

$410.48

Owl’s Nest – Modern Lakeside RetreatbrbrDiscover the perfect blend of modern design and lakeside tranquility at Owl’s Nest, a newly updated 3-bedroom home on a peaceful pond. Sunlight fills the cozy living room through a stunning lakeside wall of windows, while a fully equipped modern kitchen makes cooking a breeze. Step outside onto the wraparound deck to take in breathtaking lake views, listen to the loons, and gather around the firepit for evening relaxation.brbrThe home’s beautiful, modern touches are complemented by subtle boho charm, creating a warm and inviting atmosphere. Downstairs, the private master suite offers a separate living area, mini kitchen, and walkout patio for easy lake access. Enjoy serene sunrise views from the master suite or step directly out to the private waterfront with sandy, gradual entry — perfect for swimming or lounging.brbrFor adventure on the water, two kayaks and two paddleboards are provided to explore the calm pond at your own pace. Whether relaxing indoors, taking in the scenery from the deck, or enjoying a swim off the dock, Owl’s Nest offers a true lakeside escape.brbr2026 Rates: $360/night PEAK season; $290/night LOW season; $260/night OFF seasonbrbr- $120 cleaning fee br- Heat pump A/C in the main living room and upstairs twin bedroombr- Sheets, pillowcases, and towels are not provided (optional linen service is available) brbrFor VRBO bookings, please select no when prompted to opt out of the damage protection and travel insurance, as these services are offered directly through Krainin Real Estate after booking.

New for 2026 – Owl’s Nest | Modern Lakeside 3-Bedroom Retreat

Raymond, Maine, United States

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$755.36

Beautiful 4 bedroom , 3 full bathroom home that comfortably sleeps 8. Bedroom1: 1 king Bedroom 2: 1 queen, Bedroom 3: 2 twins. Bedroom 4 :1 twin and basement living area with twin bed. House is full of light! Spacious living room with gorgeous views of Lake Sebago. Large front deck with roll out sun shade and plenty of comfy deck furniture. Screened in side porch with table and chairs. Fully equipped modern kitchen with granite countertops. 3 full baths. Deep water off large dock. Crystal clear water with mooring available. 3 kayaks and a canoe available. Close to Frye's Leap.br*During high summer boat traffic in the area is heavy on Saturday and Sunday afternoons but quiet during the week.

Gorgeous lakefront home on Sebago Lake!

Raymond, Maine, United States

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Bath

Sleeps

$587.03

Panther Run River RetreatbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrEscape to the Maine countryside and settle down at the Panther Run River Retreat. Right across the street from the Historic Maine Fish Hatcher, this hatchery is known for making Raymond the 'home of landlocked salmon.' During your stay, take a tour of the hatchery, take peaceful walks around Hacker's Hill Preserve, and practice your swing at the Val Halla Golf & Recreation Course.brbrRight at your stay, the fun only continues when you fire up the provided gas grill, host a sweet summer barbecue, and stare out at the river. Speaking of the river, go for scenic kayak rides on the water, then house them in the nearby dock when you return.brbrInside, the sunlit living room provides a peaceful place to sit and stream your favorite TV shows and movies. When you aren't hanging out here, head for the fully furnished sunroom. The chef of your family will adore the full kitchen's cherry wood cabinetry, stainless steel appliances, and breakfast bar. Indulge in tasty treats at the breakfast bar or gather around the formal dining table for family-style meals. brbrSpacious, bright, and well-decorated the bedrooms are sure to satisfy your loved ones. Additional interior perks include partial air-conditioning and a private washer/dryer. brbrAs the sun sets on another day, head outside and enjoy dazzling starry sky views. brbrTHINGS TO KNOWbrGuests may use the dock for personal kayaks from Memorial day until the end of September.brStreaming services available with guests’ own account(s).brActive cameras outside on the driveway and doorbellbrbrIf you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. No more dogs are allowed.brParking notes: There is free parking available for 3 vehicles.brbrSecurity camera details: Ring doorbell camera and camera above the garage. brbrDock details: Small dock for swimming and non-motorized boat use, (6 foot dock)brbrbrbrDamage 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.

Waterfront home with a fireplace, grill, deck, washer/dryer, & AC - dog-friendly

Raymond, Maine, United States

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Bath

Sleeps

$235.34

Waterfront Writer's RetreatbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrEscape to the beautiful Maine wilderness and find yourself reconnecting with nature! Set up like an old-fashioned camp, this cozy cabin offers a unique destination for adventurers and outdoor enthusiasts alike. Views of Thomas Pond will dance in your vision daily as the home is nestled right along the shoreline. When you aren't gazing out at the magnificent sunrises and sunsets hitting the water, relax in the dry heat Finnish sauna, or in the outdoor shower. A canoe and kayaks are also available for your enjoyment.brbrDriving distance away from the towns of Raymond and Casco - enjoy exploring numerous parks, trails, four-season activities, and casual dining opportunities. brbrAfter a day full of adventure, whip up a delicious cocktail at the home's well-equipped wet bar before sitting down on the cool, leather sofa in the living room. Ensuring your comfort, the cabin comes equipped with central air-conditioning and a sizable bathroom.brbrAs the sunset begins to hit the water, get outside and fire up the gas grill before gathering around the firepit for campfire stories and s'mores. brbrTHINGS TO KNOWbrYou must be 26 years or older to rent this property.brStreaming services available with guests’ own account(s).brNew WIFI range extender installed.brUse of sauna is by appointment only.brPropane fire pit is available for use on site.brNew pillows and mattress are provided yearly.brThe sauna is available by appointment only and may be used once per guest stay.brbrIf you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. No more dogs are allowed.brParking notes: There is free parking available for 2 vehicles.brbrDock details: brbrbrbrDamage 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 26 years of age to book. Guests under 26 must be accompanied by a parent or legal guardian for the duration of the reservation.

Apartment

Refurbished waterfront 1950s cabin with sauna, firepit, grill & kayaks - dogs ok

Raymond, Maine, United States

1

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1

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2

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Select Dates for Price

Inviting lakefront home with private dock, sandy beach, and stunning views

Raymond, Maine, United States

Dockside DriftbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrEscape to your ideal retreat in Raymond, ME! This newly renovated waterfront home offers a private dock and sandy beach, perfect for swimming and kayaking. Whether you're seeking relaxation or adventure, this property caters to families, couples, and outdoor enthusiasts alike.brbrInside, a spacious living area awaits with modern comforts such as central AC and high-speed internet. The well-equipped kitchen features a fridge, stove, oven, and dishwasher, ideal for preparing meals enjoyed indoors or on the patio with breathtaking lake views.brbrAs night falls, gather around the firepit or unwind in the hammock with a good book. With plenty of comfortable sleeping arrangements, everyone can rest easy after a day of fun.brbrThis waterfront oasis offers more than just accommodation—it's a gateway to adventure with boating, fishing, kayaking, and hiking just steps away. Local dining, shopping, and scenic drives complete your perfect getaway. Reserve your stay today and discover the tranquility of Raymond, ME!brbrThings to KnowbrbrParking notes: There is free parking available for 4 vehicles.brbrDock details: 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.

4

Bed

3

Bath

9

Sleeps

$189.08