Vacation rentals in Freeport

Moss House: A Modern Waterfront Cabin in the Woods

Featured in VOGUE and Maine Home + Design, this modern, handcrafted cabin offers calm Atlantic views, 150 feet of shoreline, and a private dock, perfect for morning coffee, launching a kayak, or watching seals, seabirds, and passing boats. Set among tall pines, it blends Nordic and Japanese influences in a space that is calm and composed. Interiors of wood, stone, lime plaster, and concrete form a grounded, quietly expressive, and sustainably built retreat. 1hr from Portland, but a world apart.

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.

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.

The Outlet Studio, Rustic Comfort w Fireplace

Conveniently and perfectly located! Our studio is in a private building on a quiet dead end street yet walking distance to L.L. Bean, Bow Street Market, Leon Gorman Park, restaurants, breweries, live music, outlet shops, Freeport Farmers Market, the Amtrak station and all that downtown Freeport has to offer. A short drive to Wolfe's Neck State Park, Bradbury Mountain State Park, Mast Landing Audubon Sanctuary, the Desert of Maine, Winslow Park, farm stands and the beautiful mid-coast coast.

Cozy & Convenient Cumberland Guest Cottage

Make yourself at home in this quaint, private guest cottage, perfectly nestled halfway between Portland and Freeport. This detached guest cottage makes a perfect overnight spot as you make your way up the coast, or a home base as you explore Portland, Freeport and the whole breathtaking Casco Bay area. With a kitchenette, bedroom and living area, the cottage is ideal for solo travelers, couples, or a pair of friends looking for a comfortable home base while they explore southern Maine.

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!

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.

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

Serene, Spacious & Private Apt. near downtown Bath

"A bright star among Airbnbs" & "one of our favorite Airbnbs of all time" is how guests have described this spacious apartment with private entrance. Our space is a good match for quiet guests, as Erika works from home (we live upstairs). We honor guests' privacy while creating a special stay for you. LGBTQI+friendly. Max. 2 adults. No pets. Infants welcome but the apartment is not babyproof. No cigarettes on the property, but smoking (legal) weed on the porch is fine.

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

1000 sq. ft. 1BR+ Apt Close to Town & Nature

This very spacious and light filled apartment has beautiful views of a marsh and the headwaters of the Harraseeket River. It is also across the street from a 100+ acre bird sanctuary. There is a queen bed and a twin in the bedroom, a full in the large living room, and a twin in a small nook under the eaves off of the kitchen. You can put kayaks in across the street and it is a short 20 minute walk into downtown Freeport. Great year-round location.

Solar Suite surrounded by Nature

Solar suite on conservation property offers peaceful getaway. Large sitting room furnished with contemporary sofa, reading area, bedroom nook with natural latex Queen mattress on Japanese platform, kitchen island/toaster oven, mini fridge, dishes, silverware, linen napkins (please note this is not a full kitchen for preparing meals) private bath/shower. On the lower level of our home with private entrance. Cedar hot tub available.