Vacation rentals in Trickey Pond

4.86 out of 5 average rating, 14 reviews

Modern lakefront home on Sebago Lake in Maine

** New photos showcasing refreshed furnishings for 2026! ** Serene and spacious, this lakefront house has all of the comforts that make for a relaxing getaway. Looking for a more active vacation? Its ideal waterfront setting is the perfect launch point for a kayak adventure, a swim, or a casual hang on a float. [Note: AirBNB is auto-calculating a 13-min walk to Sebago Lake proper as its system does not recognize the "Sebago Cove" section of the lake. The house is lakefront w/ direct access!]

5.0 out of 5 average rating, 25 reviews

A cabin is positioned near the sandy shore of Long Lake, surrounded by tall pine trees. The sunrise casts a soft glow over the water, highlighting the cabin's exterior. A small dock is visible in the background, with the lake offering an unobstructed view.

Cabin in Naples

Cabin at Sunshine on Long Lake

You can't get any closer to Long Lake! The Cabin at Sunshine is a few short steps to the sandy bottom of this crystal clear lake. The Cabin at Sunshine was recently remodeled to give the home a relaxed, lake feeling with unobstructed views of Long Lake. All new mattresses and appliances throughout the cabin. A new Webber grill is outside for those days when you want to spend every second outside. Walk into Naples for ice cream, cocktails, shopping, entertainment, boat rentals, and dinner.

5.0 out of 5 average rating, 26 reviews

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.

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!

4.92 out of 5 average rating, 146 reviews

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

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.

4.91 out of 5 average rating, 67 reviews

A charming home nestled among trees, with a spacious deck extending from the front. Large windows offer views of the serene surroundings, while a pathway leads from the house to the water's edge. The exterior features a mix of natural elements and a carefully maintained yard.

Cottage in Raymond

The Great Escape - Picturesque Sebago Lake

Experience an intimate home with stunning Sebago Lake views. This inviting retreat features 4 bedrooms and 8 beds, ensuring a restful stay for up to 12 guests. The enormous kitchen island is perfect for gathering, whether preparing a family feast or enjoying casual conversations. Snuggle up by the propane fireplace in the living area, or spend evenings around the outdoor firepit, making s’mores under the stars. The breathtaking lake views create a serene backdrop for your vacation.

5.0 out of 5 average rating, 152 reviews

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

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!

4.95 out of 5 average rating, 43 reviews

Cottage in Naples

Sebago Pines Hideaway-Fire Pit/Beach Access/Family

Welcome to the Sebago Pines Hideaway! Located in the Sebago Pines community of Casco, this stunning retreat is the perfect place to make memories that will last forever. Enjoy the beach or grab a book and relax on the patio by day and gather by the fire with the family by night. Sebago Pines Hideway offers the perfect mix of lake life and modern living. 2 min to Sebago Pines Beach Access 10 min Naples Causeway 10 min to Sebago State Park 15 min Point Sebago Golf Course

Superhost

An open living area features large windows that provide natural light and a view of the waterfront. A wooden dining table is positioned near the window, while a comfortable seating area includes a sofa and armchair, set against a stone fireplace.

Cabin in Naples

Cabin on the Cove

Bright, open waterfront home on Sebago Cove! Enjoy swimming, kayaking, or rent a boat and park it right at our dock. Quick drive to the Causeway for restaurants and shopping. The main home features 3 bedrooms (5 beds) and 1 full bath. Lower level offers 2 bedrooms (3 beds), 1 full bath and kitchen. Family friendly and spacious. The perfect spot for summer fun and all of your winter activities with access to snowmobile trails across the lake. Close proximity to skiing!

4.83 out of 5 average rating, 53 reviews

4.96 out of 5 average rating, 124 reviews

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

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.

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.

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!