Holiday rentals in Freeport

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Top-rated holiday rentals in Freeport

Guests agree: these stays are highly rated for location, cleanliness and more.

Guest favourite

Cottage in Pownal

4.99 out of 5 average rating, 321 reviews

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.

28 Jan – 4 Feb

₹22,863 per night
Guest favourite

Tiny home in Durham

4.99 out of 5 average rating, 295 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.

11–18 Jan

₹14,106 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.

23–30 Oct

₹13,400 per night

Popular amenities for Freeport holiday rentals

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

Guest suite in Lewiston

4.97 out of 5 average rating, 188 reviews

Sanctuary in the City

31 May – 7 Jun

₹11,373 per night
Guest favourite

Cottage in Bath

4.88 out of 5 average rating, 495 reviews

Doubling Point Cottage

5–12 May

₹9,676 per night
Guest favourite

Guest house in Cumberland

4.97 out of 5 average rating, 152 reviews

Cottage Under a Crabapple Tree

25 Apr – 2 May

₹12,733 per night
Guest favourite

Tiny home in Dresden

4.96 out of 5 average rating, 160 reviews

Maplenook Tiny Cabin - A Cozy Woodland Oasis

15–22 Jul

₹9,416 per night
Guest favourite

Guest house in Portland

4.95 out of 5 average rating, 278 reviews

Beautiful large studio on the ocean.

25–30 Apr

₹13,221 per night
Guest favourite

Flat in Richmond

4.88 out of 5 average rating, 156 reviews

Designers Dream 1br Apt where class meets relax!!!

18–25 Nov

₹9,637 per night
Guest favourite

Flat in Brunswick

4.99 out of 5 average rating, 194 reviews

Charming Saltwater Farm apartment

5–12 Oct

₹10,784 per night
Guest favourite

Home in Edgecomb

4.95 out of 5 average rating, 397 reviews

Sheepscot Harbour Cottage/waterview

15–22 Feb

₹11,254 per night
Guest favourite

Guest suite in Brunswick

4.93 out of 5 average rating, 310 reviews

Art House Gallery guest suite

18–25 Dec

₹10,279 per night
Guest favourite

Cabin in Lovell

4.98 out of 5 average rating, 246 reviews

Secluded, cozy cabin nestled in the Maine woods

13–20 Sep

₹9,475 per night
Guest favourite

Guest house in Freeport

5.0 out of 5 average rating, 23 reviews

Mast Landing Cottage

18–25 Feb

₹10,762 per night
Guest favourite

Flat in Freeport

5.0 out of 5 average rating, 66 reviews

Lovely country apt. near L L Bean & hiking trails

13–20 Apr

₹12,127 per night

Quick stats about holiday rentals in Freeport

Total rentals

190 properties

Wifi availability

190 properties include access to wifi

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

8.7T reviews

Destinations to explore

  1. Airbnb
  2. United States
  3. Maine
  4. Cumberland County
  5. Freeport