Holiday houses in Freeport

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Top-rated holiday rentals in Freeport

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Guest favourite

Tiny home in Durham

4.99 out of 5 average rating, 297 reviews

Crow’s Nest Tiny House at Old Crow Ranch

The Crow's Nest Tiny House sits nestled on Old Crow Ranch, a 70-acre working livestock farm, a true example of thriving Maine farmland. You'll be surrounded by fields and pine woods in Durham, Maine. Just outside Freeport and only 30 minutes from Portland, this cozy space makes a calming retreat away from the city - for a night or for a week. Fall asleep listening to the peepers and gazing at the stars, drink your morning coffee while looking out at the cattle & chickens grazing in the fields.

20–27 Mar

$312 NZD per night

Guest favourite

Cottage in Topsham

4.95 out of 5 average rating, 212 reviews

Cozy waterfront home on Merrymeeting Bay.

Our cozy cottage is the perfect romantic getaway or quiet retreat in any season. Located on a private rd with scenic waterfront view. Guests can enjoy sitting on the dock (May- October) or the jetty, watch the eagles and Osprey, use our kayaks, do some fishing, walking or biking. Sit by the propane fueled fireplace on a chilly night. Brunswick, home of Bowdoin College and a # of great restaurants and unique shops is just 5 mi. Travel by bus or train to/from Boston. Portland is @ 30 min away.

24–31 Dec

$310 NZD per night

Guest favourite

Guesthouse in Harpswell

4.95 out of 5 average rating, 429 reviews

Harpswell Studio on Waterview Property! Lobster!

Attached Cottage Style Studio! Clean, comfy, spacious, colorful and bright! Easy access to Harpswell’s 216 miles of coastline via coastal trails, lovely side roads, small beaches and preserves. Too many trails to count in the surrounding area! Fresh lobster and seafood! Two spectacular state parks with expansive beaches within a scenic 35 minute drive! Just 45 minutes (33 miles) to Coastal Maine Botanical Gardens! Saturday check-in may be available before mid June. Please message us.

1–8 May

$248 NZD per night

Guest favourite

Home in Freeport

4.99 out of 5 average rating, 163 reviews

"The Cozy Cottage in the heart of Freeport Village

Our cozy and tranquil one bedroom cottage is located in the heart of Freeport Village. Enjoy a short walk to restaurants, shops, and outlets – including the L.L. Bean flagship store steps away! Our clean and tastefully decorated cottage offers all you need and awaits your arrival. Wifi & Cable TV in Living Room & Bedroom. We THE COTTAGE DOES NOT ACCOMADATE CHILDREN UNDER THE AGE OF 12 FOR SAFETY REASONS. WE DO NOT ACCEPT GUESTS WITH NO REVIEWS ON AIRBNB. NO PETS DUE TO SEVERE ALLEGIES.

13–20 Jan

$272 NZD per night

Guest favourite

Apartment in Freeport

5.0 out of 5 average rating, 130 reviews

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

9–16 Jan

$353 NZD per night

Guest favourite

Loft in Freeport

4.97 out of 5 average rating, 194 reviews

Cozy & Private Studio Apartment (Pet Friendly!)

Recently renovated studio apartment, very cozy, with a private side yard and entrance, kitchenette and TV (Cable, 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!

17–24 Jun

$277 NZD per night

Guest favourite

Cabin in Freeport

4.98 out of 5 average rating, 469 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

16–23 Jun

$335 NZD per night

Guest favourite

Guest suite in Brunswick

4.93 out of 5 average rating, 313 reviews

Art House Gallery guest suite

Welcome come stay at our 2 Bedroom guesthouse/duplex convenient to everything,walking distance to downtown 15 minutes to Freeport 25 minutes to Portland.smoke-free,private entrance ,WiFi,washer/dryer,full kitchen,pet friendly,40"TV smart tv with Netflix and Hulu, 5 minutes to Bowdoin College! Free eggs from our chickens included! And while in season help yourself to our vegetable garden. Fire pit area grill and outdoor dining area. We recycle and compost!

1–8 Dec

$197 NZD per night

Guest favourite

Apartment in Freeport

4.91 out of 5 average rating, 195 reviews

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 twin 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.

13–20 Dec

$225 NZD per night

Guest favourite

Guest suite in Freeport

4.97 out of 5 average rating, 116 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.

3–10 Oct

$236 NZD per night

Guest favourite

Home in Freeport

4.94 out of 5 average rating, 205 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.

28 Sep – 5 Oct

$293 NZD per night

Guest favourite

Guest suite in Freeport

4.95 out of 5 average rating, 194 reviews

Weather's Edge, Freeport

Come enjoy the historic charm of South Freeport. This antique home and cozy accommodation await you, featuring a private entrance, private room, private full bath, t.v. with cable, and wi-fi. This is a second-floor room, accessed from a dramatic original (steep) staircase, and is conveniently located in an area of lovely homes, with Freeport Village just five minutes away.

18–25 May

$135 NZD per night

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Freeport holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Stay near Freeport's top sights

Wolfe's Neck Woods State Park123 locals recommend

L.L. Bean Factory Store270 locals recommend

Desert of Maine25 locals recommend

Wolfe's Neck Oceanfront Camping5 locals recommend

Buck's Naked BBQ14 locals recommend

Freeport Village Station65 locals recommend

Other great holiday rentals in Freeport

Guest favourite

Tiny home in New Gloucester

4.95 out of 5 average rating, 124 reviews

Tiny house in the Birch Grove

23–30 Aug

$302 NZD per night

Guest favourite

Cottage in Pownal

4.99 out of 5 average rating, 322 reviews

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

16–23 Mar

$532 NZD per night

Guest favourite

Home in Freeport

4.85 out of 5 average rating, 249 reviews

Home On Pond in Woods - Guest Suite

30 Sep – 7 Oct

$165 NZD per night

Guest favourite

Guesthouse in Georgetown

4.9 out of 5 average rating, 136 reviews

Island Alchemy Cottage

16–23 Jul

$242 NZD per night

Guest favourite

Loft in Brunswick

4.97 out of 5 average rating, 180 reviews

The Douglas Park Loft

9–16 Mar

$246 NZD per night

Guest favourite

Loft in Brunswick

4.92 out of 5 average rating, 501 reviews

Downtown Hideaway-Loft HotTub Modern Clean Private

2–9 Feb

$261 NZD per night

Guest favourite

Loft in West Gardiner

4.98 out of 5 average rating, 110 reviews

Cozy, Efficiency Apartment with Hot Tub

30 Jan – 6 Feb

$233 NZD per night

Guest favourite

Guesthouse in Freeport

5.0 out of 5 average rating, 23 reviews

Mast Landing Cottage

26 Aug – 2 Sep

$299 NZD per night

Show all

Quick stats about holiday rentals in Freeport

Total rentals	190 properties
Wi-Fi availability	180 properties include access to Wi-Fi
Rentals with dedicated workspaces	70 properties have a dedicated workspace
Pet-friendly rentals	80 properties allow pets
Family-friendly rentals	80 properties are a good fit for families
Total number of reviews	8.8K reviews

Holiday houses in Freeport

Top-rated holiday rentals in Freeport

Tiny home in Durham

Cottage in Topsham

Guesthouse in Harpswell

Home in Freeport

Apartment in Freeport

Loft in Freeport

Cabin in Freeport

Guest suite in Brunswick

Apartment in Freeport

Guest suite in Freeport

Home in Freeport

Guest suite in Freeport

Holiday rentals for every style

Houses

Apartments

Cottages

Popular amenities for Freeport holiday rentals

Stay near Freeport's top sights

Other great holiday rentals in Freeport

Tiny home in New Gloucester

Cottage in Pownal

Home in Freeport

Guesthouse in Georgetown

Loft in Brunswick

Loft in Brunswick

Loft in West Gardiner

Guesthouse in Freeport

Quick stats about holiday rentals in Freeport

Total rentals

Wi-Fi availability

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Destinations to explore