Holiday houses in Kennebunk Pond

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Top-rated holiday rentals in Kennebunk Pond

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

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Top Guest favourite

A modern cabin with an A-frame shape is illuminated by warm lights, surrounded by tall trees. In front, a fire pit with wooden chairs invites gatherings, while a hot tub and sauna are visible nearby, contributing to the outdoor relaxation space.

Cabin in South Berwick

5.0 out of 5 average rating, 322 reviews

Romantic A-Frame cabin in the woods

Stay at Hidden Pines Cabins. Modern cabin tucked privately in the forest. Loaded with modern amenities make it perfect for a romantic getaway. Unwind in the hot tub looking up at the sky full of stars. Take a Sauna while being surrounded by nature all around. Relax by the fire pit. Located in the majestic forest of mount agamenticus, the extensive trail system is off our road. Short drive to the Ogunquit/ york beaches, outlets at Kittery and near Portsmouth, Dover and Portland restaurant scenes.

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Home in Kennebunk

4.78 out of 5 average rating, 9 reviews

Alewive House | Restored 1860 Farmhouse on 5 Acres

Welcome to Alewive House — a lovingly restored 1860 New England farmhouse where original character and historic charm have been brought thoughtfully back to life. Set on 5.5 private acres at one of the highest elevations in Kennebunk, this classic property offers sweeping views of rolling fields and open countryside, breathtaking sunrises and sunsets, and the rare feeling of wide-open space — just minutes from the coast. 15 min to Kennebunkport's Dock Square 20 min to Beaches 30 min to Portland

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Top Guest favourite

A wooden treehouse with large windows and a spiral staircase is surrounded by lush green trees. The structure is elevated, allowing for a view of the forest floor, which is covered in natural earth tones from fallen leaves and pine needles.

Treehouse in Sanford

4.91 out of 5 average rating, 601 reviews

Luxury Year-round Treehouse with private hot tub

The Canopy is one of 5 luxurious tiny homes that make up Littlefield Retreat, a tranquil woodland village of 3 treehouses and 2 hobbit houses – each with its own private hot tub and dock. To see all five dwellings, click on the photo to the left of “Hosted by Bryce”, then click “Show more…”. This 15-acre forest retreat on Littlefield Pond offers our guests an experience that feels like a trip up to the woods of northern Maine, but is closer to home and to all the attractions of southern Maine.

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Guest favourite

Home in Lyman

4.98 out of 5 average rating, 49 reviews

Family Friendly Kennebunk Pond Lakefront Retreat

Time of Wonder is a family-friendly vacation rental in coastal Maine, ideal for up to 6 guests. Nestled on Kennebunk Pond, this 3-bedroom, 2-bath home features a fire pit and hammock by the lake. Relax by your private dock while listening to loons and enjoying breathtaking sunsets. With two paddle boards available, lake fun is at your fingertips. Discover the charming towns of Kennebunk and Kennebunkport, along with their beautiful beaches. Plus, Kennebunk Pond is great for ice fishing too!!!

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Guest favourite

A serene outdoor space features a private dock extending into a pond, surrounded by vibrant greenery. The decked area in front of a modern home includes blue seating and two boats, inviting relaxation and enjoyment by the water.

Cabin in Lyman

4.89 out of 5 average rating, 61 reviews

Eagle Island on Wadleigh Pond

Enjoy the best of Maine without the long drive. Completely Remodeled in 2024 with private fenced yard. Beautiful views of our pond and private Eagle islands. Great fishing, kayaking, Bird Watching, Gorgeous sunsets. Many Bald Eagles frequent the pond and trees of Eagle Island. 3 kayaks and a paddle boat are onsite for guest use “Use at own risk”. Enjoy the Fire pit on cool New England nights. Close to Kennebunkport, Biddeford, Portland. 3 Security cameras in use outside the home for safety.

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Top Guest favourite

A fire pit area is surrounded by four wicker chairs with red cushions, positioned on a stone patio. The grass is well-kept, leading to the calm lake that reflects the trees and colorful foliage in the background.

Home in Sanford

5.0 out of 5 average rating, 30 reviews

Tall Pines Lakeside Cottage

Take a break and unwind at this peaceful lakefront cottage on Estes Lake in Southern Maine. Only 10 miles from I-95 and 90 miles from Boston. Enjoy swimming, fishing, canoeing and campfires steps away from our newly built 2 bedrooms, 1 bath farm style cottage. Beautiful public beaches in Kennebunk, Wells, Ogunquit, are 13 to 20 miles away. Maines largest city Portland and Portland Jetport are within 30 miles. Come enjoy a wonderful lake experience and all that Southern Maine has to offer.

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Top Guest favourite

An aerial view displays a colonial home surrounded by vibrant autumn foliage, set on an expansive lawn. The nearby Kennebunk River curves through the landscape, bordered by trees. The property includes a serene setting with open spaces and distant houses visible among the greenery.

Home in Arundel

4.95 out of 5 average rating, 107 reviews

Classic, calm river view & centrally located home

We are happy to share with you our coastal, colonial home set on eight acres along the Kennebunk River. Enjoy our quaint, warm home just 5 min to the beach and 3 minutes to Cape Arundel Golf Club. Our 4 bdrm, 2.5 bathroom suits short or long term stays. The location is ideal: 6 min from Kennebunkport, 15 min from Biddeford, and 30 min from Portland or Portsmouth! We hope to make you feel at home with the morning birds chirping and the calmness of the river just in back of the property.

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Top Guest favourite

A spacious corner sectional sofa is adorned with multiple throw pillows, positioned beneath tall, triangular windows that invite natural light. The surrounding walls feature a soft grey hue, and the wooden flooring adds warmth to the seating area.

Home in Alfred

4.96 out of 5 average rating, 28 reviews

Rustic Forest Escape

Escape to our woodland wonderland: a 3-bed, 2.5-bath hideaway where birds handle the morning alarm. Start the day with an infrared sauna, freestanding tub, aperitivo on the deck at sunset, and end the night drinking hot chocolate in front of a cozy fireplace. Fast Wi-Fi, full kitchen, and driveway parking keep both kids and grown-ups satisfied. With a lake nearby for water sports, a classic New England summer adventure awaits you! Please contact Denise:954 673 6631, in case of emergency.

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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, 150 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!

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Top Guest favourite

A large window frames the ocean view, where waves gently roll towards rocky outcrops. A cozy seating area, featuring a leather sofa and a wooden coffee table, is positioned to allow for a serene observation of the changing tides.

Home in Cape Elizabeth

5.0 out of 5 average rating, 36 reviews

"Periwinkle" ~ a Charming Oceanfront Cottage

Breath taking views await you at Periwinkle, a charming cottage by the sea. Located in a private community where you’ll enjoy a common beach/cove and a beautiful stroll out onto the point where you can enjoy the sun rises and sunsets … The cottage sits on its own little private cove where you can hunt for sea glass! There are long sandy beaches nearby for strolling and swimming and plenty to do and see in the Portland area, just 5 miles or so from the cottage!

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Guest favourite

Cottage in Lyman

4.83 out of 5 average rating, 120 reviews

Cozy Waterfront Cottage w/ Private Dock & Kayaks

Waterfront getaway! Enjoy this cozy cottage year-round, set right on the pond with your own private dock for swimming and floating. Relax by the fireplace under twinkle lights or explore nearby trails for hiking, ATV, or snowmobiling. Take advantage of the kayaks and canoe, or unwind indoors with Smart TVs and DVDs. Just a short drive to Kennebunkport’s beaches, shops, and restaurants—perfect for a peaceful retreat.

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Guest favourite

A sandy beach stretches into the distance, visible from a coastal property. The exterior features a light-colored shingle design, with a covered porch offering seating. Green shrubbery lines the foreground, creating a natural border against the ocean backdrop and clear blue sky.

Home in Wells

4.88 out of 5 average rating, 142 reviews

Drakes Island Beach Front Breathtaking Property !

Ocean views from Kennebunkport to Cape Neddick and a gorgeous half mile sandy beach right outside your door! Watch the sunrise and the sunset over the sandy Drakes Island shores. Enjoy daily walks on the beach or take a walk on the peaceful trails nearby alongside the Rachel Carson Wildlife Refuge & Laudholm Farm, and go to town for restaurants, arcades and more fun. It doesn’t get better than this !

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