Family-friendly holiday rentals in Raymond

Relax by a Quiet Lake

Charming lakeside cottage only 29' from the water on Panther Pond, w/65' of private waterfront. The cottage is a 3-season, classic L.C. Andrews log-sided Maine summer lake home. Cozy atmosphere and a wonderful enclosed porch with amazing waterfront views. Enjoy fishing off the dock, hiking, canoeing, campfire, and exploring surrounding areas. Air conditioning units will ensure your comfort on warm summer nights and high-speed internet will keep your devices connected. Furnishings are family mix.

Luxury Year-round Treehouse with private hot tub

The Canopy is one of 5 luxurious tiny homes that make up Littlefield Retreat, a tranquil woodland village of 3 treehouses and 2 hobbit houses – each with its own private hot tub and dock. To see all five dwellings, click on the photo to the left of “Hosted by Bryce”, then click “Show more…”. This 15-acre forest retreat on Littlefield Pond offers our guests an experience that feels like a trip up to the woods of northern Maine, but is closer to home and to all the attractions of southern Maine.

Waterfront Gem walkable to Restaurants!

Waterfront Oasis on Pettingill Pond. You couldn't get any closer to the water, it's steps away. There are 3 Kayaks, and a paddleboat, firepit and dock for guest use! This a great spot for swimming and watersports! This home has been newly renovated, the effect results in a simple, stylish, comfortable space for guests to enjoy. Walk to Franco's Bistro for from Scratch Italian food, or Bob's Seafood for a fish taco! This is a piece of paradise on sweet Pettingill Pond in the heart of Windham.

Cozy Family Home with Beach Access

Complete remodel with access to a private beach, boat ramp, and dock. This charming open floor plan ranch features 3 bedrooms, 1 bath, fireplace, 1st floor laundry, granite countertops, new appliances, and a lovely porch. Enjoy a large sandy beach area with picnic tables and kayak rack. The water gradually deepens, perfect for families. Close to 2 marinas, a restaurant, and a sandwich shop. Professionally remodeled with all new systems and finishes. Essentially a new home in a prime location.

Dreamy Post&Beam Hideaway Near Portland & Freeport

Escape to a dreamy timber-frame cottage tucked in Maine’s woods! Soaring beams, radiant-heated floors, a king loft bed, and a crackling fire pit await. Sip coffee on one of the two decks, hike Bradbury Mountain (3 minutes away), shop Freeport (10 minutes away), or dine in Portland (20 minutes away)—then return to your cozy hideaway under the stars. Full kitchen, vaulted ceilings, radiant heat floors, private driveway, fire pit and peaceful forest views make it the perfect year-round retreat.

LUX Designer Private Waterfront Hot Tub - Secluded

Escape to a luxurious, privately designed glass-walled waterfront cabin on 3+ secluded acres along the Crooked River in Naples, Maine. The river wraps around, offering total privacy, your own sandy beach, dock with direct Sebago Lake access, and state park minutes away. Unwind in the year-round hot tub, outdoor shower, hammocks, or by the see-through fireplace. Luxe bath with heated floors, huge walk-in shower w/ scenic window. AC, pets welcome. Perfect peaceful retreat—come recharge!

Crow’s Nest Tiny House at Old Crow Ranch

The Crow's Nest Tiny House sits nestled on Old Crow Ranch, a 70-acre working livestock farm, a true example of thriving Maine farmland. You'll be surrounded by fields and pine woods in Durham, Maine. Just outside Freeport and only 30 minutes from Portland, this cozy space makes a calming retreat away from the city - for a night or for a week. Fall asleep listening to the peepers and gazing at the stars, drink your morning coffee while looking out at the cattle grazing in the fields.

Cottage with private beach access to sebago lake

The Raymond Cottage is the perfect place for Families, couples and nature lovers. Two Bedrooms, fitted with Queen size beds. The House has been freshly renovated in january/february 2023, with all new furniture. 5 minutes from sebago lake, shopping and dining. Just 30 minutes from Portland, this is the perfect place for your Maine vacation. Access to a little private sand beach just 5 min walking distance down our road, it is shared with all on rd. Brand new shower in march 2025

Rustic, cozy cabin on Sebago Lake. A hidden gem.

Step out of the screened in patio to lakeside relaxation. Dive into crystal waters, snorkel or float with a cool beverage. Kayak or canoe out to Turtle Cove and enjoy the wildlife in this natural waterway teeming with birds to include our resident Blue Heron, ducks, geese, and loons who make this place their home. We have the fortune of bald eagles in several tall pines. Turtles sunning on doting rocks and lily pads in bloom greet us each day. It is a natural water landscape.

Spacious Lakehouse +Private Dock+Firepit+Kayaks

Welcome to Salmon Point Lodge on beautiful Panther Pond in Raymond, Maine! Nestled on 3 serene acres shared with the friendly owners, this spacious 2,800 sq. ft. home offers the perfect mix of rustic charm and modern comfort. Whether you’re looking for a peaceful getaway or an outdoor adventure, this property has it all including: -Private Dock -Fire Pit -Complementary Kayaks -BBQ Grill -Indoor Fireplace -Ping Pong Table & Board Games -Washer & Dryer -Fully Equipped Kitchen

Raymond Sebago Cabin | Private EV+ Fire Pit

Escape to Rustic Knotty Pine Gettaway, a true Maine retreat in the pines of Raymond. Start mornings with coffee on a private screened deck in the treetops, end days by the fire pit under the stars. 2 bedrooms, 1.5 baths, king +queen beds, fast 150 Mbps WiFi, free firewood. Ev charging 2 minutes to Raymond beach and 15 minutes to Sebago State Park. 5 minutes to shopping and restaurants.

Jackson Winter Wonderland - Wildcat/Attitash

Nestled in the picturesque town of Jackson, this charming log cabin offers a one-of-a-kind getaway experience. Surrounded by the stunning White Mountains and situated alongside the Ellis River with a refreshing swimming hole, this property is the ultimate retreat for those seeking tranquility and natural beauty. Located between Wildcat + Attitash for the perfect ski vacation.