Holiday rentals in Pleasant Lake

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Top-rated holiday rentals in Pleasant Lake

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite

A serene lakeside scene is presented with two dark green Adirondack chairs positioned around a fire pit on a grassy area. A wooden dock extends into the lake, with a small boat resting beside it, surrounded by trees that frame the tranquil view.

Cottage in Raymond

5.0 out of 5 average rating, 97 reviews

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.

Top guest favourite

Home in Oxford

5.0 out of 5 average rating, 245 reviews

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.

Guest favourite

A wooden dock extends over the calm water, leading to a serene sunset view. The sun sets behind the distant hills, casting warm hues across the lake. An umbrella stands at the edge of the dock, offering shaded seating areas.

Home in Casco

4.96 out of 5 average rating, 27 reviews

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!

Guest favourite

Home in Naples

4.97 out of 5 average rating, 197 reviews

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!

Top guest favourite

A wooden dock extends toward calm water, with a gentle sloping pathway leading down from the boathouse. The clear water reveals stones at the bottom, while green trees frame the picturesque lakeside view.

Guest house in New Gloucester

4.9 out of 5 average rating, 175 reviews

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!

Top guest favourite

Two wooden chairs are situated on a dock overlooking a calm pond surrounded by dense trees. The water reflects the sky and greenery, creating a serene backdrop. A sense of tranquility is conveyed through the peaceful atmosphere of the natural setting.

Home in Oxford

4.93 out of 5 average rating, 147 reviews

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.

Top guest favourite

The entrance features a combination of corrugated metal and natural wood siding, creating a modern aesthetic. A wooden porch with a small wooden overhang leads to a glass-paneled front door framed by two narrow windows. Gravel pathways enhance the natural setting.

Cottage in Otisfield

5.0 out of 5 average rating, 44 reviews

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.

Top guest favourite

The exterior of the A-frame cabin is showcased, featuring a unique wooden facade and metal roof. Sunlight streams through tall triangular windows, illuminating the surrounding wooded area. A gravel path leads to the entryway, enhancing the cabin's connection to nature.

Cabin in Freeport

5.0 out of 5 average rating, 152 reviews

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!

Top guest favourite

An aerial view captures a serene lakeside scene surrounded by lush greenery. The expansive blue water of the lake reflects the sky, while the home is nestled among the trees, providing a sense of tranquility and seclusion.

Home in Raymond

4.97 out of 5 average rating, 32 reviews

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

Top guest favourite

A cozy fire pit area is situated near the water's edge, surrounded by tall trees. Adjacently, five colorful adirondack chairs offer seating for gatherings. A serene view of the lake and a private dock can be seen in the background, providing a tranquil backdrop.

Chalet in Naples

4.96 out of 5 average rating, 124 reviews

The Chalet~ 4 bed Lakefront Family Vacation

Welcome to your secluded slice of paradise on the shores of Sebago Lake! Nestled amidst towering pines and overlooking the tranquil waters of Seabgo Cove, our 4-bedroom waterfront chalet promises a serene escape like no other. Whether you're seeking adrenaline-pumping thrills from the local excursions, or peaceful moments surrounded by nature and a book, The Chalet offers endless opportunities for unforgettable experiences and cherished memories in the heart of Naples.

Guest favourite

The living area features high, wooden ceilings with exposed beams and large windows, allowing natural light to flood the space. A stone fireplace serves as a focal point, while a cozy seating area is complemented by a dining table surrounded by red chairs.

Home in Naples

4.94 out of 5 average rating, 140 reviews

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!

Top guest favourite

A charming two-story lake house is surrounded by tall trees, with a sandy area leading to the water. Several kayaks and chairs are visible by the lakeside, inviting relaxation under the clear sky.

Home in Poland

4.94 out of 5 average rating, 49 reviews

The Hidden Gem

Relax with the whole family at our peaceful lake house, loaded with charm inside and out. Kayaks, paddle boards, canoe, 1 propane grill and 1 black stone griddle, long dock with Adirondack chairs, fire pit with wood and SO much more! Fully equipped kitchen, bedding, board games, books.. the list is endless. Just bring groceries and any extras you may need and leave the rest up to us. Come and relax, leave your worries behind!