Family-friendly vacation rentals in Freeport

Cozy Sunny 1BR • Quiet • Near Bowdoin• Route 1/295

Warm, comfortable 1-bedroom apartment in a quiet Brunswick neighborhood — ideal for winter stays, remote work, or extended visits. Just one mile from Bowdoin College with quick access to Route 1 and I-295, this bright and private space offers the perfect balance of peaceful surroundings and convenient location. Surrounded by trees and fresh Maine air, the apartment feels tucked away while remaining minutes from downtown Brunswick, Freeport outlets, coastal walks, and seasonal outdoor activities.

Freeport Village Sunny Studio

Privacy and nature on the edge of the Village with a deck onto the yard, laundry, and small kitchen. You'll enjoy sitting out on the deck listening to the birds and you may see a deer, woodchuck, or chipmunk. Very quiet residential street. Walk to trails (5 min, Bow Street Market (5 min), LLBean (5min), restaurants (5-8min), and Amtrak (4min). Have the best of both worlds! We have an extensive guidebook to the area available through the Airbnb platform. Take a look! (Note: No microwave.)

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!

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

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.

Modern Brunswick Tiny Home near Bowdoin & Downtown

A lofted bed space with additional optional pull out couch fitted with ergonomic foam mattresses. This space has air conditioning as well as heat and amazing natural light. Brand new bathroom with rain shower head! A full kitchen with mini fridge, separate freezer space, oven, stove and coffee/tea supplies. Centrally located in Brunswick, and quiet! Right across from Bowdoin’s Whittier Field, and 10 minute walk to Maine Street.