Holiday rentals in Kennebunkport

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.

Birch Sea

This new, very private apartment attached to our home is in a quiet and picturesque environment minutes away from Dock Square. It's great for couples, solo adventurers and families with one child. If you are seeking to spend the day at one of the beautiful Kennebunk beaches they are just minutes away. We are committed to environmental sustainability and the apartment is powered by solar energy. A new outdoor hot tub was recently installed in February, 2024! We look forward to your visit!

NewBuilt/HotTub/Great Location-4 min Kennebunkport

Follow us on IG @anchorunwind. Welcome to Mama Bear's House! Perfect girlfriends' getaway or to celebrate a special someone. Sit back and relax in our brand new and fully equipped stylish home just 5 minutes away from Kennebunkport's Dock Square. Spend time reading and sipping a fresh grounded coffee on our cozy egg chair, looking in our peaceful backyard while the sunset closes another memorable chapter of your vacation. Enjoy the firepit with hot cocoa and s'mores or fall for a cornhole game!

Lower Village Lofts •North• Steps to Dock Square

The Lower Village Lofts *North* is a newly renovated large studio apartment located in the heart of the action - just steps from Dock Square (downtown Kennebunkport) and 1/2 mile to the beach! This unit features a brand new fully equipped kitchen, all new designer and higher end furnishings, and a custom built-in room divider complete with an electric fireplace, armoire, and 50" smart TV. The bedroom area has a new king bed with luxurious bedding, black out shades, and an additional smart TV.

Oceanfront w/ Stunning views and Private Deck☀️🏖

Welcome to the Beach House on the Rocks, your very own oceanfront retreat! This beautiful, 1350 sq ft house is nestled right next to the ocean. With panoramic views and the ocean just steps away, you won’t forget this one of a kind experience. Tucked away in the hidden gem of Camp Ellis, you’ll enjoy a lively beach scene in the summer and a tranquil retreat in the off season. Just a short trip away to Old Orchard Beach and 30 min to Portland you’ll never be in need of fun activities.

Romantic New England Historic Schoolhouse c1866

Winner of Maine Homes Small Space Design Award 2023 We are located on the private 80-acre Shapleigh Pond in the Southern Maine, an hour from Portland and two hours from Boston. Experience a bygone era in this restored Schoolhouse circa 1866 with many original details such as oversized glass-paned windows, wood plank floors, chalkboards, tin ceiling and more. Modern amenities such as fireplace, private hot tub, fire pit, gas BBQ and access to our pool (June-Sept), pond and tennis court.

Farmhouse Retreat Upstairs | Walk to Downtown|

Experience the charm of our beautifully renovated 1870 farmhouse, a spacious upper unit Kennebunk vacation rental, offering comfort and relaxation, just a 5-minute walk from downtown!! Enjoy easy access to local coffee shops, restaurants, the farmers market and popular Garden Street Bowling Alley. Ideal for a cozy, convenient getaway. Need more space? Check out our profile to book the full-house rental, perfect for up to 8 guests. Beach Parking Permit for Kennebunk Beaches included!!

1760 Morrill Farm House-5 Minutes to Kennebunkport

Welcome to the 1760 Morrill Farm House, your idyllic sanctuary for your iconic Vacationland experience. Just a 5 minute drive to Kennebunk and Kennebunkport villages, Mother’s, Middle and Gooch’s beaches. Free beach pass provided. PLEASE NOTE: This unique space has very low ceilings and may not accommodate people over 6 feet tall comfortably. PLEASE NOTE: Unit 2 only has one designated parking spot. Any extra cars in your party must park on the side of the road next to the bushes.

Farmhouse Experience in a Beachside Community

2025 Summer Rentals: 7 night min requirement (Friday Check-in) / Inquire for alternative dates. Enjoy being equidistant between Dock Square and Cape Porpoise, where you be immersed in a world of top chefs, fine wines, beautiful homes, acclaimed artists, and the quintessential oceanfront charm of Kennebunkport. Relax in this inspired barn house restored design with modern touches in a farm to table community. Weather the storm with our newly installed generator.

Cape Porpoise Private Guest Suite with King Bed

Come relax in the guest suite of our new modern farmhouse, one mile from Cape Porpoise's village town centre in Kennebunkport. Enjoy a private entrance and outdoor seating space/ fire pit overlooking a wooded lot. The 1000 sq. ft. space is bright and roomy. It has a king-sized bed with tv, kitchenette, office area and a 50 inch smart tv in the comfy living room. Walk outside our home and find 27 miles of interconnecting conservation land trails.

350 Steps to Gooch’s Beach! Water Views

Ideal location 350 steps to beautiful Gooch’s beach. Easy walk or short drive to Kennebunkport's Dock Square with shops and restaurants. This is the upper floor of a 2 floor, 2 unit building. Sunny and cheerful w/open floor plan, gas fireplace, and large back deck. WiFi and live streaming tv are included. Outdoor shower. Beach chairs/towels provided. Walk to beach & town. 7 day minimum, Saturday check in/check out July through August 2026.

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 !