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, 599 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.)

4.99 out of 5 average rating, 416 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, 245 reviews

Waterfront Private Apartment just 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, 246 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, 197 reviews

The kitchen features white cabinetry and a modern stainless steel stove. A round wooden table, set with blue placemats, includes a vibrant floral centerpiece. Natural light streams through the window, illuminating the space, which is equipped with essential appliances and ample counter space.

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

4.97 out of 5 average rating, 526 reviews

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.

Cabin in Freeport

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, 100 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, 238 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 spacious sitting area is visible from the entrance, featuring a contemporary sofa and a grand piano. Natural light floods the room through large windows, with artwork adorning the walls and decorative elements placed thoughtfully on shelves.

4.98 out of 5 average rating, 173 reviews

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.

4.88 out of 5 average rating, 107 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, and 2 kayaks are available for guest use. 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 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.

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, 165 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.

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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, 44 reviews

Studio Apartment in Freeport

4.92 out of 5 average rating, 12 reviews

A modern kitchen is characterized by white cabinetry and stainless steel appliances. A large farmhouse sink is centered beneath a window, which provides natural light. Hardwood flooring adds warmth, while a brick stove in the corner complements the space.

Apartment in Freeport

Cozy Studio in Downtown Freeport

5 out of 5 average rating, 64 reviews

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.

Cabin in Freeport

The Maine Frame: Cozy Retreat | Freeport Woods

5 out of 5 average rating, 40 reviews

A spacious studio retreat is showcased, featuring a cozy bed with warm wood accents. A seating area with comfortable chairs and a soft rug complements the space. A small dining table is also visible, alongside natural light streaming through a window.

Guesthouse in Freeport

Flying Point Retreat near Wolfe's Neck Center

4.97 out of 5 average rating, 39 reviews

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.

Cabin in Freeport

Chickadee A-Frame

4.93 out of 5 average rating, 167 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