Holiday houses in Freeport

4.99 out of 5 average rating, 396 reviews

Cottage in Pownal

Upscale Timber-Frame Cottage, Shop/Dine/Hike/Bike

Relax and unwind at this cozy post-and-beam cottage in a woodsy setting. Complete with all the modern amenities you will feel at home after exploring all that Maine has to offer. At day’s end ascend to the loft bedroom for a great night's sleep. Please note the current Maine travel restrictions: https://www.maine.gov/covid19 This custom post and beam cottage is brand new. Designed by John Libby, one of the most respected timber frame builders in New England, (www.housesandbarns.com) this space was thoughtfully designed and meticulously built specifically for your enjoyment. This cottage resides on the owner’s property, but is sited on its own two acres nestled among a beautiful stretch of Maine hardwood forest. Accessible via its own private driveway and surrounded by acres of pristine forest, it is the perfect place to relax among nature. No matter the season the exposed weathered Douglas Fir beams of the building will both welcome you and wrap you in a feeling of comfort and contentment. This complete home has all of the amenities. The kitchen includes natural unpolished granite countertops and brand new appliances including a stainless steel gas oven/range, dishwasher and refrigerator. The whitewashed walls of the hallway and bathroom provide a more modern feel, while showcasing all the wonderful knots of the Maine white pine from which it was milled. An easy-to-access, low/no step corner shower complete with floor to ceiling tile and an oversized vanity make time in the bathroom a pleasure. The open concept makes for a natural flow through the space and the sitting area comes complete with a queen sofa bed, TV and a gas fired wood-stove. The vaulted ceilings rise 22’ above the floor providing a spacious and beautiful feel. Radiant heat in the finished concrete floors make the space cozy and keep your feet warm. Oversized and lit stairs lead to the loft where you’ll find a king sized bed providing the opportunity for a great night’s sleep. Large windows make you feel as though your sleeping in the tree tops…come Fall this Oak and Maple forest comes alive with color. A ceiling fan keeps you cool, in the Summer and moves the heat around come Winter. Enjoy the beautiful outdoors on either the front or back deck, or from your own personal fire pit complete with granite bench. Don’t forget the s’mores! Guests have access to the post and beam cottage as well as the immediate surrounding area. We ask that the property boundaries are respected and that the guests do not go past the rock wall or onto the main house property or neighboring properties/horse farm. The post and beam cottage is on the same property as our primary residence but has it’s own driveway and is situated in a private clearing surrounded by beautiful forest. We will usually be available to welcome you personally and are happy to meet new people and make new friends but we also respect our guests privacy as we expect the same in return. Thank you! This post and beam cottage is in the small town of Pownal, 20 minutes from the wonderful restaurants, sights, and sounds of Portland. It's a 10-minute drive to Freeport and the L.L.Bean flagship store. Bradbury Mountain State Park is two miles away.

4.73 out of 5 average rating, 579 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, 139 reviews

Apartment in Yarmouth

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.

4.97 out of 5 average rating, 236 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, 237 reviews

Loft in Freeport

Cozy & Private Studio Apartment (Pet Friendly!)

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, 181 reviews

Barn in Freeport

Cozy Maine Barn Hideaway- 2nd Floor Apartment

Welcome to our spacious 1000 sq. ft. Maine barn apartment! 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

4.91 out of 5 average rating, 116 reviews

Tiny home in Bowdoinham

Sweet Fern Cabin on Merrymeeting Bay

Nestled in the woods on 2.5 waterfront acres where the Muddy River meets Merrymeeting Bay. The cabin is 350 square feet of simple living with a panoramic view. There is a three season hot water outdoor shower and wood burning stove with plenty of wood included. Kitchen is fully stocked with cooking supplies and has off grid cold water sink. Outbuilding with composting toilet is right out the back door. Kayaks and stand up paddle board are available to rent for an additional fee.

4.97 out of 5 average rating, 510 reviews

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

4.92 out of 5 average rating, 227 reviews

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.

4.98 out of 5 average rating, 160 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.

4.93 out of 5 average rating, 153 reviews

Guesthouse in Brunswick

Modern Brunswick Cottage 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.

4.92 out of 5 average rating, 253 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.

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Popular amenities for Freeport holiday rentals

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Other great holiday rentals in Freeport

5 out of 5 average rating, 47 reviews

Waterfront Cottage in Freeport

BrianRating, 5 stars2 weeks ago

Beautiful location on the water with stunning views, tranquil and peaceful with plenty of osprey and bald eagle sightings (there is a nest across the bay on Pettingill Island visible from the property). The house is very well-appointed and well-decorated. Irena was very communicative and responsive, and the house directions are clear and complete. We would stay there again. Thank you!

4.98 out of 5 average rating, 89 reviews

Farm stay in Brunswick

Brunswick Farm Stay

TomRating, 5 stars2 weeks ago

Seth and Maura’s place was perfect for my needs. The apartment is roomy, comfortable, and bright. I felt right at home preparing meals, relaxing on the couch, and getting good nights’ sleeps in the large and cozy bedroom. Access to the trails on the property is a wonderful bonus, with winding loops through a variety of habitats and tons of bird activity. To top it all off, the Saturday morning farmer’s market on the property is a wonderful way to provision yourself for your stay, with lots of local providers of veggies, meats, cheeses, breads, and flowers. I also enjoyed watching and hearing the farming activity, from mowing fields to loading trucks with produce. Overall, a great experience that I hope to repeat.

Superhost

4.8 out of 5 average rating, 35 reviews

Amazing location! Cheerful home near LL Bean

EmilyRating, 5 stars8 months ago

Such a lovely, cozy spot! We stayed for two nights with toddlers and our dog and everyone was very happy there.

5 out of 5 average rating, 6 reviews

Barn in Durham

Convenient studio apartment for Maine travels

MattRating, 5 stars1 week ago

Laura was a great host. We stayed at her place for a night to split up our drive from MA to Bar Harbor. We almost didn’t want to leave! Very clean, comfortable and easy check in. Laura was also super helpful and responsive and even gave us a great list of things to do in Acadia. We 100% recommend her and her place, you won’t be disappointed!

5 out of 5 average rating, 22 reviews

Cabin in Freeport

Chickadee A-Frame

BijouRating, 5 stars2 weeks ago

If you want to find solitude, this is the place to go. Set in the woods, 10mt drive from Freeport, the A frame cottage was just the place to chill. You could use it as a launching pad for Portland, New Brunswick and Freeport. Bow Market in Freeport offers a wide range of food and beverages.

5 out of 5 average rating, 49 reviews

Freeport Village Barn Studio

Stanley JRating, 5 stars2 weeks ago

Lauren was an excellent host ! Quick responses and very helpful. The place was awesome, very spacious and comfortable. You can’t beat the Freeport location close to lots of outlets and restaurants and Maine Beer Brewery. Highly recommend. I would definitely use again.

4.93 out of 5 average rating, 27 reviews

Forest House in Freeport Village

GeorgiosRating, 5 stars5 months ago

We had a wonderful stay. Melissa's house is charming and spacious and very tastefully decorated. We felt right at home from the first, and loved the fact that it was an easy walk to all of the wonderful attractions of Freeport. Melissa was very easy to communicte with and made sure that everything went smoothly, even offering to arrange snow removal after an unexpected (and beauteful) snow fall. We could not have asked for anything more during our winter holiday with two toddlers and teenageer. Thank you Melissa!