Holiday houses in Freeport

1820s Maine Cottage with Garden

Enjoy a cozy shipbuilder's cottage in Bath, Maine. This quaint apartment attached to a family home has its own entrance and contains a bedroom, a bathroom, a kitchen, and a living room with antique details that reflect its 200-year old history. Only a 15-minute walk to historic downtown Bath, a 3-minute drive to Thorne Head Preserve, and a 25-minute drive to Reid State Park and Popham Beach. Come appreciate everything MidCoast Maine has to offer! PLEASE NOTE: This apartment has steep stairs!

Sweet 1-Bedroom Apartment in Vintage Village Cape

Built roughly 200 years ago, the traditional cape housing this first-floor apartment is located on a hilltop above the Royal River, just steps from restaurants, trails, and waterfront. It's been thoroughly renovated, and features pretty much all the comforts of home—including a full kitchen with dishwasher, a wood-burning fireplace insert, an all-natural mattress (super comfy), and a clawfoot tub-equipped bathroom. Oh, and if you're bringing a third, let me know—and I'll roll in the rollaway.

Lobstermen's ocean-front cottage

Be our guests & experience the life & beauty of Midcoast Maine. Relax & enjoy the views, warm up in the sauna or go for a refreshing dip. The cottage is part of an over 100 year old working lobstering, and now oyster farming property we call, Gurnet Village. Located right on historic Route 24, we are conveniently situated between Brunswick & the islands of Harpswell. All rooms have ocean views. The tidal beach & the floating dock (May-Dec) is ideal for seasonal fishing, lounging & swimming.

Dreamy Post&Beam Hideaway Near Portland & Freeport

Escape to a dreamy timber-frame cottage tucked in Maine’s woods! Soaring beams, radiant-heated floors, a king loft bed, and a crackling fire pit await. Sip coffee on one of the two decks, hike Bradbury Mountain (3 minutes away), shop Freeport (10 minutes away), or dine in Portland (20 minutes away)—then return to your cozy hideaway under the stars. Full kitchen, vaulted ceilings, radiant heat floors, private driveway, fire pit and peaceful forest views make it the perfect year-round retreat.

Cozy & Private Studio Apartment

Recently renovated studio apartment, very cozy, with a private side yard and entrance, kitchenette and TV (Roku with Netflix, Disney Plus, Hulu and Amazon). Very comfortable queen size bed with floor space for kids, if desired. Fantastically located just over a mile from beautiful Winslow Park's walking trails and beach, four miles south of downtown Freeport's shopping and 15 miles north of the popular city of Portland. Housebroken and well behaved pets welcome to join their humans!

Fully Updated Airy Historic Home in South Freeport

Conveniently located 5 minutes from downtown Freeport, 20 minutes from Portland Jetport, and 20 minutes from downtown Portland. This newly renovated, charming, and sunny 200 year old home is perfect for your Maine getaway. It is a fantastic home-base for exploring Southern and Midcoastal Maine while enjoying close proximity to shopping in Freeport and Portland's award-winning restaurants and attractions as well as beautiful beaches, islands, museums, lighthouses, and much more.

Charming Victorian farmhouse 1880's bedrooms-2

Victorian farmhouse 1880's Stay in an "era gone by". Private 2 bedroom. Original hardwood floors. Original pocket doors. Sleeps 6. Has living room, kitchen, dinning area 1 bathroom with tub , study area. Charming town, population 4000+. smoke free house. Private keyless entry. The blue door. Free wifi, cable, roku. Has keurig coffee maker with free coffee, dishes, pots, pans, silverware, nu-wave cooktop, toaster, microwave, fridge, pack n play. Queen beds. W & D private.

Cozy Maine Barn Hideaway- 2nd Floor Guesthouse

Welcome to our spacious 1000 sq. ft. Maine barn guesthouse! This bright and comfortable retreat is the perfect base for exploring all that Maine has to offer. Enjoy the fully-appointed kitchen, equipped with everything you need. The quiet bedrooms feature memory foam beds for a restful sleep, and the bathroom boasts a spacious shower. Please note that we have a no-pet policy due to allergies. Book your stay today and experience the best of Maine! Registration #: STRR-2021-24

Spacious Cozy Home in Freeport, ME

Come enjoy Freeport, Maine in this beautiful home. One mile from the downtown shopping district and the L.L. Bean flagship store. This two family home is being rented as a single family home, giving you the benefit of two kitchens and two living rooms. Perfect for families and groups of friends. The two sides are connected via a door similar to adjoining hotel rooms. For winter guests our pond is great for skating and we have a variety of skates available upon request.

Modern cozy cottage in historic coastal Maine

Contemporary, newly-renovated cottage between Portland and Freeport. Spotless interior w/ full kitchen, Netflix/AppleTV+, premium Tuft+Needle bed, and washer/dryer. EV charging available. Walk down Main Street to shops, restaurants, and the scenic Royal River. Easy drives to downhill skiing and iconic beaches, Portland's renowned restaurants, LL Bean flagship, and top-rated Maine Brewing. Half way between Boston and Sugarloaf. Your ideal base for Maine adventures.

Cozy Cottage-Near Harbor & Park

Bailiwick Cottage is a cozy, private cottage that looks south down Freeport (Harraseeket) Harbor in Freeport, ME. It is a 4 season accommodation that is close to Freeport shopping, Portland eating, and the Adventure Schools of LL Bean. The cottage sits approximately 50 yards from our main house, has its own parking space and patio, and offers the ability to come and go as you wish. We have had 12 honeymoons in the cottage. Freeport Registration # STRR-2022-59

Freeport Escape – LLBean | Fire Pit | 3 King | A/C

The Freeport Escape – A charming early 1900s home with modern amenities. Located in the heart of Freeport, walkable to shopping, restaurants, breweries, and the Amtrak station. Set on a private corner lot, enjoy the fire pit, porch grilling, and spacious outdoor area. Cozy up by the indoor fireplace in cooler months. Perfect for families, couples, and friends. 🛏️ 3 King Beds | Family-Friendly | ❄️ A/C | 🔥 Fire Pit | 🪵 Indoor Fireplace 📍 STRR-2022-82