Holiday rentals in Pleasant Lake

Lovely Lakefront Cottage - Book Your Fall GetAway!

Whether you’re craving a peaceful retreat or a winter adventure, this lakefront cottage has everything you need to create unforgettable memories. Cozy up by the fire, snowshoe the lake, or simply soak in the serene beauty of the season. Embrace the charm of winter on the lake, the perfect getaway for families, couples, or solo adventurers. Don't wait for summer to fall in love with this hidden gem. NOTE: Winter & Spring guests should be comfortable navigating winter weather/seasonal conditions.

The Modern Lakehouse

This modern lakehouse is situated on Hogan Pond in Oxford Maine. Here you can stay with all the comforts of a beautiful lakehouse built in 2020 while being feet from the water. This is a great place to vacation whether you prefer the private sandy beach, the A/C inside complete with Smart TV cable and Wifi, or the hottub! Sip a drink at the bar while watching the game or use the grill on the deck but be sure to use the built in sound system to play your music throughout the house and deck.

Waterview Lake House

Welcome to Waterview Lake House! Please enjoy the private 200ft water frontage! Parker Pond is located in Casco, Maine. This peaceful lake is great for boating, fishing or soaking in the beautiful sun. A large dock, boat access, amazing westerly sunset views and a kayak/canoe are just some of the amenities! With infinite options, you can just relax or explore the beauty of Maine! This lovely and spacious 3 bedroom lake house will have you and your group wanting to return year after year!

Tri-Lake Escape: Brandy Pond

Tri-Lake Escape offers the ultimate waterfront getaway with direct access to Brandy Pond, Long Lake, and Sebago Lake. This charming retreat is perfect for families, couples, and outdoor enthusiasts looking to relax and explore. Enjoy stunning lake views, a private dock, and endless activities, including swimming, boating, fishing, and kayaking. Unwind on the spacious deck, gather around the fire pit, or take a short drive to downtown Naples for dining, shopping, and local attractions.

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!

On the water Boathouse!

In the water! Two story boathouse. Originally built in 1939 and parked boats in until 1972. Converted to living space in the early eighties. The upstairs consist of a bedroom walk in closet and a balcony. The downstairs is a living room, kitchen and bathroom. Walk out the door to the patio , dock , and beach! You won't find anything closer to the water! The balcony is the perfect place to watch the sunset, thunderstorms, or sip your morning coffee. Watch the fish out the window!

Mirror Pond Cottage

A sweet space on a pond, this cottage is perfect for those looking for a quiet getaway. We offer swimming, kayaks and a canoe, life jackets along with a raft to float on. Endless fun in the water, with no motors to be heard. This is a quiet spot and we would hate to be responsible for ruining that. We are family friendly and kids are welcome, but please leave the party at the casino (5 minutes away)! The waterfront is sandy and shallow, perfect for young ones to splash around in.

Modern secluded cottage in the woods of Maine

Arcibello-Italian for very lovely Guest House: Secluded, modern, romantic, tranquil, newly constructed award winning design. Surround yourself in nature outdoors and original artwork indoors. 10 min. walk to Thompson Lake or 1 mile drive to our beach and boat launch. We have 2 kayaks for water activities or bring your snow shoes or cross-country skis in season. Drive to quaint local towns like Norway or Bridgton for food, shopping and hiking. Premium linens and eco-friendly products.

The Maine Frame | Modern A-Frame Cabin in Freeport

• Perfect for small families or couples, our signature A-Frame cabin features a modern interior gas burning fireplace, soaring ceilings, huge windows, stylish interiors, and all the comforts of home. • This cozy 1,100 square foot space comfortably accommodates up to four guests in two bedrooms (one with a King-size bed and the other with a Queen-size bed) and a shared bathroom. • 7 minute drive to downtown Freeport. • Proud to be ranked in the top 1% and voted Guest Favorite!

Best Ski & Lake House

Spectacular, expansive, state-of-the-art log cabin—your ultimate four-season escape. Winter ski trips (just 25 minutes to Pleasant Mountain, formerly Shawnee Peak), summer fun (beaches & watersports galore), & unforgettable year-round gatherings. Chef’s kitchen with two ovens, dining for eight + bar seating, sleeps up to 12 (with 2 king beds), two living rooms, and abundant outdoor dining & lounge space, including a playground - designed to make lasting memories!

All seasons Thompson Lake house

Experience the perfect lake getaway—where the water is just a short stroll away and the comforts of home are everywhere. Nestled just across the road from the sparkling shoreline, our home offers a peaceful escape with private, shared community beach access. Whether you want to kayak, hike, ski, fish, or simply relax, our location is convenient for exploring all Maine has to offer - no matter the season.

Family Camp at Coffee Pond, private home for 8

Very friendly and well appointed house in the woods with private lakefront access. Gradual slope down to lake; no stairs needed. We supply kayaks and a canoe with paddles and a pedal boat. We supply PFDs. The home is the perfect getaway for a quiet wooded lake experience, and also features daily singing by the loons and visits from hummingbirds. House also offers solar power to offset your carbon footprint.