Holiday rentals in Kennebunk Pond

Luxury Year-round Hobbit House w/ private hot tub

Fern Hollow 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.

Secluded Coastal Home & Cottage 3 Minutes to Beach

Escape to Thistle Pond Cottage, a peaceful coastal retreat in southern Maine. Nestled on 2 acres with pond views, lush gardens, and local wildlife, it’s minutes from beaches and Portland. Every stay begins with homemade bread from our kitchen and thoughtful, locally sourced welcome accompaniments. Weather and seasonal permitting, guests may occasionally savor a host-prepared wood-fired pizza made with fresh garden ingredients. Cozy, bright, and full of garden-to-table charm and seasonal delight.

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!!!

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.

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.

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.

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.

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!

Romantic Mirror cabin in the woods

Stay at Hidden Pines Cabins. The Mirror cabin is Maines only 3 sided floor to ceiling mirrored glass cabin. Unwind in the hot tub while looking up at the sky full of stars. Take a sauna while surrounded by nature all around. Located in the majestic forest of mount Agamenticus, the extensive trail system is off of our road. Short drive to the Ogunquit/York beaches, Outlets at Kittery and near Portsmouth, Dover and Portland restaurant scenes.

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.

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 !

Studio, listen to the loons at Bunganut Lakefront

Leisurely relax lakeside though no view from the studio. But steps away from the water. Listening to the loons watching the sunset. Yet a short ride to the ocean. A small lake so relative quiet There is a swimming platform off shore, kayaks available, along with a fire pit and BBQ grill. Soak up the sun or relax under the Weeping Willow tree on the edge of Bunganut Pond.