Holiday rentals in Cumberland County

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Top-rated holiday rentals in Cumberland County

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Guest favourite
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.
12–19 AprIndividual Host,
£248 per night
4.99 out of 5 average rating, 317 reviews
Guest favourite
Guest house in Harpswell
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! Available 1/18 and this weekend!
25 Mar – 1 AprIndividual Host,
£95 per night
4.95 out of 5 average rating, 428 reviews
Guest favourite
Guest house in Windham
Cottage on Black Brook Preserve
This charming cottage is thoughtfully furnished, it's your home away from home! Clean and cozy, one bedroom with queen size bed and full kitchen. Sit in front of the gas fireplace or on your own private deck overlooking the 105 acres of Black Brook Preserve. Take a hike, snowshoe or cross-country ski right outside your door. We now have new sofa, bed, refrigerator, stove, as well as shower and bathroom flooring.
7–14 MayIndividual Host,
£116 per night
5.0 out of 5 average rating, 213 reviews

Popular amenities for Cumberland County holiday rentals

Other great holiday rentals in Cumberland County

Guest favourite
Flat in Portland
"Percival" Penthouse Suite - Amazing Harbor Views
3–10 NovIndividual Host,
£453 per night
4.97 out of 5 average rating, 214 reviews
Guest favourite
Home in Hollis
Birch Ledge Guesthouse--Four Season Maine Getaway
19–26 AugIndividual Host,
£158 per night
4.98 out of 5 average rating, 349 reviews
Guest favourite
Guest house in Cape Elizabeth
Newly built private guest suite off Shore Road
6–13 May
£138 per night
4.98 out of 5 average rating, 138 reviews
Guest favourite
Farm stay in Gray
The Retreat at Crystal Lake Farm
10–17 MayIndividual Host,
£158 per night
4.88 out of 5 average rating, 238 reviews
Guest favourite
Barn in Portland
Garrison Cove Studio
3–10 Dec
£148 per night
5.0 out of 5 average rating, 378 reviews
Guest favourite
Tiny home in Freeport
Cozy Rock Cabin #thewaylifeshouldbe
Individual Host
4.99 out of 5 average rating, 197 reviews
Guest favourite
Guest suite in South Portland
Oceanfront with amazing views and private entrance
20–27 AugIndividual Host,
£290 per night
5.0 out of 5 average rating, 668 reviews
Guest favourite
Guest suite in Freeport
Solar Suite surrounded by Nature
1–8 NovIndividual Host,
£111 per night
4.96 out of 5 average rating, 113 reviews
Guest favourite
Guest suite in Freeport
Weather's Edge, Freeport
11–18 Aug
£84 per night
4.96 out of 5 average rating, 191 reviews
Guest favourite
Home in Cumberland
Rustic charm close to Portland
5–12 JanIndividual Host,
£173 per night
4.95 out of 5 average rating, 277 reviews
Guest favourite
Farm stay in North Yarmouth
Hobby Farm Guesthouse-17 acre trails-1 good dog OK
19–26 DecIndividual Host,
£165 per night
4.96 out of 5 average rating, 110 reviews
Guest favourite
Cottage in Falmouth
Cobb Cottage: Lake Paradise! Fri-Fri only Jun-Aug
12–19 May
£541 per night
5.0 out of 5 average rating, 23 reviews

Destinations to explore