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Villa holiday rentals in Cumberland County

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Top-rated villa rentals in Cumberland County

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Villa in Sebago

Couples Cottage Limit 4

705 - 1 Bedrooms, 1.0 Baths (Sleeps 4) OCCUPANCY LIMIT 4. Designed with a modern camp spa style the couples cottage has high ceilings, white washed pine walls and plenty of windows providing soft natural light. Beautiful designed, the cottage's great room has lots of space with views of Sebago Lake. The cottage has a full kitchen and additional lofted sleeping space accessed by a latter. The main suite has lake views, have some coffee on your private patio or relax in the modern soaking tub.

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.

Aerial view of a row of cabins set in a natural landscape, featuring a gravel path lined with trees. Each cabin has a dark exterior with contrasting yellow trim, and a small porch. The surrounding greenery adds to the serene atmosphere.
Villa in Sebago

Finch Limit 4

706 - 2 Bedrooms, 1.0 Baths (Sleeps 4) OCCUPANCY LIMIT 4. The cabin includes a private bedroom and bath, plus a common room with kitchenette. This two-bedroom cabin is a short walk to the pond side floating boardwalk. One bedroom has a queen bed, and the other bedroom is a bunk bed. Plus, a small futon in the common room. This allows for up to 4 guests. Guests will also have access to the natural pond. You can also enjoy Sebago Lake with at Nason's Beach which is a very short drive away.

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.

The image captures a sandy beach leading to Sebago Lake, with gentle waves lapping against the shore. A wooden dock extends into the clear water, providing access for boats. Multiple boats are anchored in the distance under a bright blue sky with scattered clouds.
Villa in Sebago

Camp Lindy Limit 7

252 - 4 Bedrooms, 1.5 Baths (Sleeps 7) OCCUPANCY - STRICT LIMIT 7 - NO PETS - SEBAGO LAKE BEACHFRONT. Comfortable, classic shorefront summer cottage on Long Beach. WIFI. Nice sandy beach and views of Sebago Lake from the enclosed porch. Well maintained and equipped. Four bedrooms (all on the second floor). Fireplace in livingroom. Smart TV w/internet. Deck for afternoon sunning. Dock. Walking distance to local convenience store and restaurant. Great fishing, boating and swimming.

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.

Popular amenities for Cumberland County villa rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Private villa rentals

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

Villa in Sebago

New! Northwest Eagle Nest Limit 9

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

A wooden walkway leads to the entrance of the cabin, with sunlight casting shadows across the planks. The entryway features a small set of steps and is surrounded by trees. In the background, the lake can be seen through the foliage.
Villa in Sebago

Dockside Retreat Limit 14

Villa in Bridgton
New place to stay

New! Stargazer Shores Limit 8

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

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

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

Luxury villa rentals

Villa in Sebago

New! Barker Pond Escape Limit 8

A charming cottage is visible from the dock, surrounded by trees and located on a sandy beach. A pathway leads from the dock to the front of the cottage, where outdoor seating is arranged on a patio. The sky is partly cloudy.
Villa in Sebago

Clearview Limit 6

An expansive view of Sebago Lake is captured at sunset, featuring warm shades of orange and yellow reflecting off the calm water surface. The horizon is lined with distant mountains, creating a serene backdrop against the sky filled with soft clouds.
Villa in Sebago

Grandview Lakefront Limit 9

Two lounge chairs are positioned on a wooden dock, facing an expansive view of the lake. Clear blue skies with fluffy clouds reflect on the water's surface, creating a serene atmosphere. The surrounding area offers a peaceful and open waterfront space.
Villa in Sebago

A Sense of Place Limit 17

A charming cottage with a classic design features a large screened porch, framed by an American flag. The exterior showcases light blue shingle siding and is surrounded by trees, with a sandy yard leading to a tranquil waterfront.
Villa in Sebago

Friendly Inn Limit 5

A charming two-story cottage is set amidst tall pine trees, featuring a welcoming front porch with green door and steps leading to the entrance. The surrounding area has natural gravel pathways and a shaded, serene atmosphere created by the tree canopy.
Villa in Standish

Fletcher Limit 8

The exterior of the cottage features a wooden deck leading to a gravel pathway. Sunlight filters through the trees, creating patterns on the ground. In the background, the serene blue waters of the lake are visible, enhancing the peaceful setting.
Villa in Sebago

Placyd Pines Limit 8

Villa rentals with a pool

A group of cabins is situated along a calm pond, connected by a raised boardwalk. Each cabin features a distinct black and yellow exterior. Surrounding greenery and a stone patio with a fire pit enhance the outdoor space, reflecting the tranquil setting.
Villa in Sebago

Phoebe Limit 3

A row of black cabins with distinct yellow trim is set against a backdrop of greenery. Each cabin is positioned along a pebbled pathway, surrounded by trees and natural terrain, providing a serene environment. The cabins feature sloped roofs and front porches, inviting outdoor relaxation.
Villa in Sebago

Nuthatch Limit 4

A row of modern cabins with dark exteriors and contrasting yellow accents is set among a natural landscape. Gravel paths connect the cabins, which are surrounded by greenery and trees, providing a serene and spacious outdoor environment.
Villa in Sebago

Titmouse Limit 4

A row of cabins with yellow accents is positioned along a reflective pond. A walkway connects the cabins to the waterfront, while greenery and a firepit are visible in the foreground. The setting showcases a harmonious blend of nature and cabin architecture.
Villa in Sebago

Cardinal Limit 3

A collection of cabins is arranged along a gravel path, surrounded by trees and natural landscaping. Each cabin features a black facade with yellow trim and a small porch. The setting conveys a serene and rustic atmosphere, ideal for a peaceful getaway.
Villa in Sebago

Chickadee Limit 4

A series of quaint cabins with bold yellow trim are arranged along a floating boardwalk, reflecting their vibrant colors in the calm water of the pond. Stone pathways and greenery frame the scene, enhancing the natural outdoor setting.
Villa in Sebago

Hummingbird Limit 3

A row of modern cabins is nestled among trees, each featuring a dark exterior with bright trim. A gravel path leads through the property, providing access to the cabins. Surrounding greenery offers a natural setting, enhancing the quiet ambiance of the area.
Villa in Sebago

Junco Limit 4

A series of black and yellow cabins line a floating boardwalk that extends over a calm pond. The scene is complemented by manicured landscaping and a stone patio area with a fire pit, inviting relaxation by the water.
Villa in Sebago

Robin Limit 3

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