Guesthouse holiday rentals in Scarborough

Cottage Near the Sea, private with deck

Back on the market after a hiatus, with sanded floors, fresh paint and other great updates!. Enjoy this immaculate cottage on a quiet neighborhood street in the upscale, seaside community of Falmouth Foreside. Walk to the beach, walk to the town landing waterfront, swim, ride bikes, and enjoy this charming seaside town. Ten minutes from Portland. Cottage is open concept with tons of natural sunlight. The beach is about a 7-minute walk. There’s no TV so bring your devices if you want them.

On the water Boathouse!

In the water! Two story boathouse. Originally built in 1939 and parked boats in until 1972. Converted to living space in the early eighties. The upstairs consist of a bedroom walk in closet and a balcony. The downstairs is a living room, kitchen and bathroom. Walk out the door to the patio , dock , and beach! You won't find anything closer to the water! The balcony is the perfect place to watch the sunset, thunderstorms, or sip your morning coffee. Watch the fish out the window!

Adorable 2 bedroom cabin only 50ft from Beach no.7

This quaint two-bedroom cottage sleeps up to six people and offers an open kitchen, dining, living room area with cathedral ceiling. There are two roomy bedrooms, one with a queen bed and one with two bunk beds. The bathroom offers his & her sinks, shower and whirlpool tub. Conveniences inc. Smart TV, Wi-Fi, individually controlled heat and air conditioning, fully equipped efficiency kitchenettes, and private baths. Enjoy the privacy of your own seaside cottage close to the beach!

Cozy Maine Barn Hideaway- 2nd Floor Guesthouse

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

Modern stay Westbrook Maine

Welcome to our modern 1-bedroom basement retreat, nestled in the charming town of Westbrook, just a short 3-minute drive from the Portland, Maine. With its stylish design and upscale amenities, this Airbnb offers the perfect blend of comfort and convenience for your stay in the area. The bedroom features a Queen-size bed, a queen-size pull-out sofa in the living area, accommodating additional guests comfortably in the spacious living area. There’s a $200 pet fee per pet.

Private Bungalow w/ Pool, Free Parking & Hot Tub

The Bungalow is a small, 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 beautiful garden could be in bloom. We now offer a Level 2 EV charging outlet. #AllAreWelcome

Spacious & Convenient 2 Bd/1 bath w/ Free Parking

Our home is close to everything Portland has to offer! We're a 5 minute drive from the airport, about 10 minutes from downtown, and walking distance to Thompson's Point to enjoy concerts, events, and libations. We are in a quiet, family friendly neighborhood with plenty of free parking. Our rental is a spacious 2 bedroom, 1 bath apartment above our garage with a private entrance. **PLEASE NOTE THERE IS NO KITCHEN** City of Portland License #001706

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.

Modern Brunswick Tiny Home 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.

Red Shed Cottage at Pickett Hill Farm

Red Shed Cottage is a renovated carriage house situated on the property of Pickett Hill Farm, an 1830's complex. The cottage is ideally situated to capture the essence of the rural countryside of the Lakes Region of Western Maine. Pickett Hill Farm offers splendid views of open fields, Pleasant Mountain and the surrounding forests, attracting naturalists, painters and photographers, as well as those who seek a restful vacation.

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.

Cottage Under a Crabapple Tree

Steps from extensive nature trails and wildflower meadows, this quaint studio cottage is nestled conveniently between the restaurants and breweries of Portland, the outlet shopping of Freeport, and miles and miles of rocky coastline. Perfect for a quiet Maine getaway, lodging near Cumberland fairgrounds and other local attractions, or a visit to family and friends in the area.