Vacation rentals in Freeport

A spacious deck is highlighted by a large red umbrella over a table, surrounded by four wicker chairs. Lush greenery and colorful flowering bushes create a natural backdrop, enhancing the outdoor seating area in the yard.

4.73 out of 5 average rating, 600 reviews

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.)

4.96 out of 5 average rating, 243 reviews

A landscaped entrance showcases vibrant flower beds filled with colorful blooms. Lush green grasses frame the pathway, leading to a welcoming door under a decorative light fixture. The scene reflects a serene outdoor environment, inviting guests to explore.

Loft in Brunswick

The Douglas Park Loft

The loft is a 20 X 20 space above our detached garage. Wide pine floors. 7 windows facing. Optimal for a couple. Sleep sofa is 70" x 54" so suitable for 1 adult or 2 children/teens. Sunny room w/room darkening shades. Radiant floor in the bathroom. Smart TV. Low radiation WiFi. Ethernet jack. Heat pump for heat or AC. Large under counter fridge w/out freezer but we have one in the garage. Two burner infrared cook-top. Toaster oven, Hot H2O kettle & coffee maker. Kitchen is ready for cooking.

4.99 out of 5 average rating, 418 reviews

The exterior of a post and beam cottage is shown, featuring a light wood facade and a brown shingled upper section. Two black Adirondack chairs are placed on a wooden deck, accompanied by potted plants. Large windows offer a view of the forested surroundings under a partly cloudy sky.

Cottage in Pownal

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.

A spacious bedroom is furnished with a king-size bed featuring a plaid bedding set. Two windows allow natural light to enter, complemented by a bedside lamp. Wooden accents, including a wardrobe and a small table, enhance the room's warm ambiance.

4.97 out of 5 average rating, 247 reviews

Waterfront Private Apartment only 5 min to LLBean!

Guest apartment with private entrances, king bed, pull out sofa, kitchenette, walk-in shower, and porch facing the water providing the perfect relaxing coastal Maine experience! Custom built home on 8 acres tucked away in the woods with waterfront access to Harraseeket Cove & South Freeport Harbor, great for kayaking! Located 5 minutes from LL Bean and Freeport's many shops, restaurants, bars, etc. Wolfes Neck State Park and its stunning coastal trails and forests are less than a mile away.

4.97 out of 5 average rating, 248 reviews

A spacious studio apartment features slanted ceilings accentuated by wooden beams. A queen bed is dressed in soft bedding, positioned near a kitchenette with modern appliances. The room is adorned with a rustic charm, complemented by light teal walls and vintage decor items.

Loft in Freeport

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!

5 out of 5 average rating, 198 reviews

Barn in Freeport

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 private 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

A cozy cottage is surrounded by greenery, featuring a combination of stone and wood accents. Large windows allow natural light to enter, while a welcoming entryway is flanked by blooming shrubs. The landscaped yard offers a peaceful setting among the trees.

4.97 out of 5 average rating, 528 reviews

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

A charming blue Victorian-style house is set on a spacious corner lot, surrounded by trees displaying autumn colors. A curved driveway leads up to the entrance, where manicured shrubs flank the walkway, enhancing the inviting façade of the home.

4.99 out of 5 average rating, 101 reviews

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

4.92 out of 5 average rating, 239 reviews

Two vintage-style homes are set against a backdrop of tall trees under a clear blue sky. One home is slightly elevated, showcasing a classic white exterior with dark shutters, while the other features a wraparound porch and larger windows, blending harmoniously with the natural landscape.

Apartment in Freeport

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 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.

A comfortable living space showcases a round dining table surrounded by four chairs. A cozy sofa and two patterned chairs are positioned to create a welcoming seating area. Natural light filters through the glass doors, which lead to an outdoor setting. Artwork decorates the walls.

4.92 out of 5 average rating, 264 reviews

The Outlet House, Comfortable Cottage

Conveniently and perfectly located! Our cottage is 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, 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 and the beautiful mid-coast coast.

4.88 out of 5 average rating, 108 reviews

A charming barn-style apartment is framed by a well-maintained garden, featuring a variety of plants and colorful flowers. The driveway leads up to the entrance, with trees providing a natural backdrop to the serene setting.

Guesthouse in Freeport

Harraseeket Estuary Loft Apartment

Great 2nd floor apartment in barn building in beautiful setting in Freeport Maine- Quiet and peaceful, very comfy space- 5 minutes from downtown Freeport and a mile (ish) from Wolfe Neck State Park. Property is off the Harraseeket River. Completely private space. Kitchen fully furnished - wonderful Bow St. Market is down the road and a great place to stop for great food and beverages.

A bright living space features large windows that invite natural light. A light-colored sofa is positioned next to a minimalist table. An open kitchen with modern seating is visible, with light wood accents and a clean design on display.

4.95 out of 5 average rating, 168 reviews

Spacious costal 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.

Vacation rentals for every style

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Cabins

Kick off your hiking boots at these rustic lodgings

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Freeport vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Freeport

Aerial view of a cottage nestled among lush green trees, with a panoramic view of Casco Bay and its islands beyond. The spacious yard is bordered by natural foliage, providing a serene backdrop for the waterfront property.

5 out of 5 average rating, 51 reviews

Waterfront Cottage in Freeport

A modern kitchen is equipped with a stainless-steel microwave and stove beneath a stylish backsplash. The countertop features a sink and invites meal preparation. A comfortable nook with a raised twin bed can be seen in the background, surrounded by decorative plants.

4.98 out of 5 average rating, 46 reviews

Studio Apartment in Freeport

The exterior of the A-frame cabin is showcased, featuring a unique wooden facade and metal roof. Sunlight streams through tall triangular windows, illuminating the surrounding wooded area. A gravel path leads to the entryway, enhancing the cabin's connection to nature.

5 out of 5 average rating, 66 reviews

The Maine Frame: Cozy Retreat | Freeport Woods

The A-Frame retreat is surrounded by snow-covered ground and tall trees. The exterior features large glass windows that invite natural light. A cozy porch is visible, with two wooden chairs and winter equipment nearby, creating a welcoming entrance to the home.

4.98 out of 5 average rating, 40 reviews

Chickadee A-Frame

4.92 out of 5 average rating, 169 reviews

A cozy living area features a comfortable gray sofa arranged near a light wooden coffee table. A large TV displays a streaming service, while natural light enters through expansive windows adorned with soft curtains. A small kitchenette is visible in the background.

Guesthouse in Brunswick

Modern Brunswick Tiny Home near Bowdoin & Downtown

A bright sleeping area features a queen bed with light bedding. A large mural depicting a serene beach scene is displayed on one wall, while a window with ocean views is dressed in navy curtains. Natural light enhances the calm atmosphere.

4.92 out of 5 average rating, 12 reviews

Charming Coastal Suite

4.92 out of 5 average rating, 552 reviews

A bright kitchen features a central island with bar seating, surrounded by modern cabinetry and stainless steel appliances. Large windows provide natural light, highlighting the rustic dining table, and wooden beams draw attention to the vaulted ceiling.

Home in Yarmouth

Beautiful Coastal Maine Getaway

The A-frame cabin features a striking sloped roof and a large glass wall, allowing natural light to flood in. Surrounded by tall trees, the cabin is nestled in a serene wooded setting, offering a peaceful retreat.