Holiday rentals in Kennebunk

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.

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.

Bass Cove Point Guest Apt Water Access Built 2025

Extraordinary guest house with beautiful water views. Nautical Maine coastal decor. 15-minute walk to the center of town. Newly built 2-bedroom apartment in 2025. Private entrance & balcony. Unmatched amenities: bikes, kayaks, picnic areas with grill, fire pit, lawn chairs, children's playhouse & indoor play cubby. Rick has very severe asthma, so we cannot allow pets. Our goal is to provide one of the best value rentals in Kennebunkport. Experience beauty & peace at Bass Cove Point. Jan & Rick

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.

Custom Kennebunk Studio Apartment

Come experience southern Maine in its most colorful season! Our private, peaceful studio is the perfect retreat for travelers looking for a cozy getaway. Just minutes from Kennebunk beaches and Dock Square in Kennebunkport, you’ll be surrounded by fall foliage, charming shops, great dining and winter ice skating. Nestled in a beautiful natural setting, you'll have a chance to spot wildlife wandering through our backyard forest right from your morning coffee spot on the studio's outdoor deck.

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!!

Fair Winds Cottage~1 mi to beach~

Our home, a renovated 1930’s Maine summer cottage, is located 1 mile from Kennebunk beaches and 1.5 miles from dining and shopping in Kennebunkport’s Dock Square. Close to golf, nature trails and only a 1/2 mile from the Mousam River for fishing and kayaking, it’s a great location to take in all southern coastal Maine has to offer. The cottage provides plenty of outdoor space, so come relax, dine on the back deck and take in the night sky with s'mores by the fire pit.

Ocean/Beach Unique Views: THE New England !

QUIET NEIGHBORHOOD, WELCOME TO FAMILIES! GAS FIREPLACE ! Classic architectural details all sited on an enviable ocean/beach location. An alluring home, lovingly maintained for 110 years, encompasses the true understated elegance of the era in which it was created. Amidst the 3,500 sq ft+, find 6 gracious bedrooms accented by 4 and a half baths, updated granite kitchen, pantry, glassed in front porch with mesmerizing views of the ever-changing sea.

Four Corners Studio Guest House

This is a newly renovated studio cottage perfect for couples or a single person. Room for a port a crib for a small child. This cottage is surrounded by an expansive yard and treeline. You'll be just under two miles from several great dining options including some fantastic seafood restaurants. You won't want to miss out on that famous Maine lobster! And for adventures on the water, the Kennebunkport marina is only two miles from your front door.

Downtown Coastal Charm Cottage in Kennebunk

Welcome to your home away from home in the heart of downtown Kennebunk! This charming coastal retreat offers a perfect blend of comfort and convenience, just steps from shops, restaurants, and scenic trails. Enjoy a fully equipped kitchen, cozy living space, and peaceful bedrooms. Whether you're here for a beach day, a lobster roll, or a quiet escape, this home is the ideal base for exploring the best of Kennebunk and coastal Maine.

Sandpiper

Discover the idyllic Maine retreat you've been dreaming of with our Sandpiper cottage nestled in The Coastal Village on Nine. Just moments away from Downtown Kennebunkport & Kennebunk's Lower Village, this cottage is a blend of tranquility and convenience, where joyful memories await your arrival. Don't just vacation—embark on a journey that you'll treasure forever.

HotTub/5min to K-port, Pet friendly, @anchorunwind

Follow us on IG @anchorunwind. Escape to a hidden gem nestled in the heart of the Kennebunkport area, where modern comfort meets nature's serenity. Our cabin offers an unforgettable vacation experience. ✭"...A must stay location. The host’s were very helpful and genuine..." ✭"...We’ve travelled all around the world and this is in our top 3 Airbnbs we’ve stayed in."