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Guesthouse rentals in Cumberland County

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in Cumberland County

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

Superhost
Guesthouse in Portland
Beautiful large studio on the ocean.
Our large, light, 2nd floor studio is airy and modern with a deck overlooking the garden, ocean and sunrise. We love to welcome guests to share our beautiful property so if you'd like to book please introduce yourselves and let us know about who is coming and some hopes for your trip. We are caring, unobtrusive hosts who value getting to know our guests a little beforehand. We think we have the best of both worlds here - the peace and beauty of Casco Bay, yet 5 minutes to the center of town.
$110 per night
Superhost
Guesthouse in Portland
Romantic Bungalow w/Hot Tub & Parking
The Bungalow is a private, luxury en-suite out-building on the property of the historic Chapman House. The space includes TV, fridge, microwave, and coffeemaker, access to the seasonal pool, and year-round shared hot tub. We are owner-operated. Relax outside on the lawn or the patio, at a picnic table (in season), one of the fire pits, or under the fir tree. Emily's beat beautiful garden could be in bloom. We now offer a Level 2 EV charging outlet. #AllAreWelcome
$98 per night
Superhost
Guesthouse in Cape Elizabeth
Newly built private guest suite off Shore Road
Newly built cozy above-garage guest suite with private entrance on dead end street. Bright & airy space, thoughtfully designed in charming, cozy neighborhood full of young families. Access to large network of trails in the 200 acre Land Trust and walking distance to beautiful cobblestone beach. Conveniently located to the shops and restaurants in town and minutes from the iconic Portland Head light located in Fort Williams park.
$99 per night

Family-friendly guest house rentals

Superhost
Guesthouse in Harpswell
Harpswell Studio on Waterview Property! Lobster!
$102 per night
Superhost
Guesthouse in Topsham
Brunswick Riverfront Garden Cottage
$125 per night
Superhost
Guesthouse in Portland
The Carriage House at Libbytown
$155 per night
Superhost
Guesthouse in Falmouth
Cottage Near the Sea, private with deck
$283 per night
Superhost
Guesthouse in Scarborough
Smith Cottage Higgins Beach
$150 per night
Guesthouse in South Freeport
South Freeport Village Barn
$125 per night
Guesthouse in Hollis Center
Moment's Peace Farm Guest House
$150 per night
Guesthouse in Wales
Lakeside, private, Maine experience.
$300 per night
Guesthouse in Old Orchard Beach
Location Location @ Tami Lyns Place
$199 per night
Superhost
Guesthouse in Cape Elizabeth
Salty Air in Cape Elizabeth | Portland | Beaches
$130 per night
Guesthouse in Old Orchard Beach
1 Block to the Beach!
$210 per night

Guest house rentals with a patio

Superhost
Guesthouse in Freeport
Discover Minglewood; a peaceful couple's getaway
$175 per night
Superhost
Guesthouse in Yarmouth
Private Guesthouse in the Woods
$210 per night
Superhost
Guesthouse in Windham
Robyn's Nest; A Maine getaway
$109 per night
Superhost
Guesthouse in Bridgton
Cozy apartment on private road close to everything
$180 per night
Superhost
Guesthouse in Yarmouth
Sunny guesthouse in coastal Maine
$159 per night
Superhost
Guesthouse in Old Orchard Beach
Fun and Sun Cozy Cabin-short walk to beach
$53 per night
Superhost
Guesthouse in Cape Elizabeth
Ocean House Retreat - Family & Group Friendly
$250 per night
Superhost
Guesthouse in Brownfield
The Forested Bohemian . Tiny home/ tree house
$120 per night
Superhost
Guesthouse in Portland
Cozy guesthouse on Peaks Island by the ocean
$145 per night
Superhost
Guesthouse in Oxford
Camp in the woods in a luxury RV camper
$120 per night
Guesthouse in South Portland
Willard Beach Guest House Minutes from Everything!
$150 per night
Guesthouse in Scarborough
Guest house, dead end Prouts Neck, Scarborough
$237 per night

Guest house rentals with a washer and dryer

Superhost
Guesthouse in Naples
Downtown Naples guesthouse. Steps from causeway
$149 per night
Superhost
Guesthouse in Cape Elizabeth
Cape Foliage, Sunset, Tranquil, LobstA
$132 per night
Superhost
Guesthouse in Hiram
1BR cozy, luxurious getaway @ Krista's Guesthouse
$225 per night
Superhost
Guesthouse in Bridgton
Escape to the lake!
$180 per night
Superhost
Guesthouse in Gorham
Cozy 2BR retreat min toUSM&Sebago
$160 per night
Superhost
Guesthouse in West Bath
Spruce Ledge Boathouse
$175 per night
Superhost
Guesthouse in Westbrook
Red Barn Retreat
$150 per night
Superhost
Guesthouse in Bridgton
Bridgton Brick House Airbnb
$179 per night
Superhost
Guesthouse in Portland
Bayside Heights
$482 per night
Guesthouse in Naples
Long Lake Waterfront Cabin
$200 per night

Destinations to explore