Villa holiday rentals in Cumberland County

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Top-rated villa rentals in Cumberland County

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A rustic cottage is set among trees, featuring a wooden exterior and a wheelchair-accessible ramp. The scene captures a grassy area leading to the sandy beach, where lakefront seating can be seen in the background. Natural light brightens the surroundings.
Villa in Standish

Harmon's Beach Limit 5

109 - 1 Bedrooms, 1.0 Baths (Sleeps 5) OCCUPANCY LIMIT 5- Pet friendly - SEBAGO LAKE BEACHFRONT. Rustic one bedroom cottage with a large sandy beach. Great spot for getting away from it all. Lots of outside seating to enjoy the views and watch the kids play in the sand. The bedroom has a Full bed. There is a twin bed in the front room and a futon in the living room. One dog w/permission and an additional $125 pet fee. Waterfront Description: Beautiful sandy beach - safe spot for children.

Villa in Sebago

New! Northwest Eagle Nest Limit 9

368 - 3 Bedrooms, 3.0 Baths (Sleeps 9) OCCUPANCY LIMIT 9 - Waterfront home has 3-bedroom 3 bath. This stunning waterfront property offers the perfect blend of serenity and modern living. Prime waterfront location on Northwest River Road with direct access to Sebago Lake. Open concept living and dining area with breathtaking views of the water. Expansive deck overlooking the lake. Easy access to boating, fishing, and swimming right from your backyard. Waterfront/Lot Description: Flat Lot.

A cottage exterior is shown, featuring wooden shingles and large windows that provide natural light. Two blue adirondack chairs are positioned on the lawn, alongside a picnic table on a flat grassy area, surrounded by trees and under a clear blue sky.
Villa in Windham

Boomfish Limit 5

518 - 2 Bedrooms, 1.0 Baths (Sleeps 5) OCCUPANCY LIMIT 5 - A waterfront 2 Bedroom 1 Bath on Highland Lake in Windham. Enjoy lake living while being less than 30 minutes from Portland. The cottage has an open living space with views of the lake from the living room and kitchen. Both bedrooms are on the main floor with full beds. There is also a loft with 2 twin beds. A nice-sized flat lot with a fire pit near the water. Shallow entry is great for swimming. Also enjoy the 2 kayaks provide.

Villa in Bridgton
New place to stay

New! Stargazer Shores Limit 8

380 - 4 Bedrooms, 2.0 Baths (Sleeps 8) OCCUPANCY LIMIT 8 - 4-bedroom, 2 bath home located in the desirable Christmas Tree Shores community on Highland Lake. A short walk away from a sandy association beach with great swimming. 2 bedrooms and 1 full bathroom on the 1st floor. One bedroom with a King bed. The other bedroom has Full bed. 2 bedrooms on the 2nd floor. One bedroom has a Full bed. The other has 2 Twin beds. Enjoy volleyball, fishing, and great swimming at the association beach.

The cottage exterior features a single-story design with large windows allowing for ample natural light. A well-maintained lawn surrounds the structure, and a patio area is visible with comfortable seating set against a backdrop of tall trees.
Villa in Sebago

Mary's Lakeview - Limit 10

MARY'S LAKEVIEW 4 Bedrooms,1 Bathrooms OCCUPANCY LIMIT 10 guests - This 4 bedroom 1 bath cottage has a large yard, views of Sebago Lake, and just 0.2 miles from Nason's Beach. Your rental comes with a free walk on pass to Nason's Beach. All the living area is on the 1st floor. A open floor plan combines the living room, dining room, and kitchen. 2 bedrooms with king beds. The 3rd bedroom has a futon. The 4th bedroom has 1 twin bed and 1 full. There is also a sleeper sofa in the foyer.

A view of the charming house situated among tall trees, accessible by a set of stairs leading up from the sandy beach. A wooden dock extends into the water, with a small boat nearby. Outdoor seating areas are present on the beach, enhancing the inviting setting.
Villa in Standish

Sandy Cove Escape Limit 8

335 - 3 Bedrooms, 2.0 Baths (Sleeps 8) OCCUPANCY- LIMIT 8 - 3-bedroom 2 bathroom with a large sandy beach. One bedroom on the main floor with a Queen and twin bed. There are 2 bedrooms on the 2nd floor. One bedroom with a full bed. The other bedroom upstairs has a Queen bed and 2 twins. There is a full bathroom on the 1st and 2nd floor. The very large lot with plenty of sitting areas to enjoy the views of the lake. The large sandy beach is one of the biggest we have in our inventory.

A rustic cottage is nestled among trees at the water's edge, surrounded by colorful foliage. Sunlight shines through the leaves, casting reflections on the clear water. A wooden dock extends into the tranquil lake, enhancing the serene atmosphere.
Villa in Sebago

Whip Poor Will Limit 5

WHIP POOR WILL 1 Bedrooms,1 Bathrooms sleeps 5 OCCUPANCY LIMIT 5 - ONE PET OK with $125 fee - PEABODY POND SHOREFRONT. What a spot! Loads of privacy at this cottage that sits literally at the water's edge. A perfect getaway spot. Listen to the cry of the Loons and watch beautiful sun and moon rises. Screen porch, large stone fireplace, open living/dining area, well equipped kitchen. Lovely view, relax and listen to the brook that borders the property. Nice dock and swim float.

Villa in Standish
New place to stay

New! Cove Overlook Limit 6

538 - 3 Bedrooms, 2.5 Baths (Sleeps 6) OCCUPANCY LIMIT 6 - 3-bedroom 2.5 bath. Just steps away from shared waterfront access with a swim float and a shared dock. You also have access to a larger sandy beach a short walk away. Enjoy spectacular views of Sebago Lake from most of the rooms in the house including all the bedrooms. This new home was built in 2019 and has a lot of very nice finishes. The three bedrooms are on the 2nd floor. The main suite has an attached bath.

A firepit made of large stones is situated near the water, with remnants of wood and ash visible. The tranquil lake reflects greenery from trees along the edge. A dock is seen in the distance, leading out over the calm water.
Villa in Sebago
5 out of 5 average rating, 3 reviews

Eva's Place Limit 7

578 - 4 Bedrooms, 3.0 Baths (Sleeps 7) OCCUPANCY LIMIT 7 Waterfront home has 4-bedroom 2 bath. The home has great finishes with a dock on the Northwest River. Direct access to Sebago Lake. Sit around the firepit with views of the water. 3 heat pumps provide AC for the home. Views of the water from the kitchen and living room. 2 bedrooms and 1 bath downstairs. 2 bedrooms upstairs with a Jack and Jill bathroom. 2 kayaks and 1 canoe provided. Fishing poles also provided.

The lakefront property is set against a backdrop of tall pine trees, featuring a grassy yard that gently slopes to the water’s edge. Colorful adirondack chairs are arranged along the shore, complementing the clear water with a sandy bottom.
Villa in Bridgton

Tremont Limit 10

TREMONT LIMIT 4 Bedrooms,2 Bathrooms (sleeps10) OCCUPANCY LIMT 10 - - WOODS POND SHOREFRONT. Lovely lakefront contemporary with all the conveniences of home. Absolutely NO PETS in or on the property due to serious owner allegies. Well equipped and nicely appointed open concept living for vacation gathering. Four bedrooms, 2 1/2 baths. Spacious open living/kitchen/dining area. Great open lake views from the living areas and the master bedroom. Dishwasher. Washer/Dryer.

A rustic shorefront cottage is positioned on a sandy beach, with a wooden walkway leading to the entrance. Surrounding trees offer gentle shade, while clouds drift across a bright sky overhead. The peaceful waters of Sebago Lake are visible in the background.
Villa in Standish

Limberlost Limit 6

LIMBERLOST 2 Bedrooms,1 Bathrooms (sleeps6) OCCUPANCY LIMIT 5- STRICT LIMIT OF 4 OCCASIONAL DAY GUESTS - SEBAGO LAKE BEACHFRONT. Pleasant, yet rustic, shorefront cottage on absolutely beautiful beach on the west shore of Sebago Lake. Picnic table on the screen porch overlooking the water, Nice quiet location. Pretty view of Sebago. WiFi, High speed internet and basic cable. Great spot! DOG CONSIDERED WITH $125 PET FEE Waterfront/Lot Description: beautiful sandy beach.

The exterior of the house showcases a striking red facade with large windows that allow natural light to flood the interior. A spacious deck is featured at the front, furnished with seating for relaxation. A pathway leads to a well-maintained yard surrounded by lush greenery.
Villa in Frye Island

Unusual Latitude Limit 7

342 - 3 Bedrooms, 2.0 Baths (Sleeps 7) OCCUPANCY LIMIT 7 This centrally located 3 bedrooms, 2 bath home on Frye Island is close to all the wonderful amenities that Frye Island has to offer. 9-hole golf course, tennis courts, pickle ball courts, ballfields, cafe and general store. Best of all there are 14 wonderful community beaches to enjoy on Sebago. The large sandy beach 6 is the closest to the house and is less than a 3-minute walk away.

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