Guesthouse holiday rentals in Scarborough

Cozy Sunny 1BR • Quiet • Decks• Bowdoin • Midcoast

Bright, comfortable 1-bedroom apartment in a quiet Brunswick neighborhood — perfect for relaxing spring, summer, and fall visits. Just one mile from Bowdoin College with quick access to Route 1 and I-295, this bright and private space offers the perfect balance of peaceful surroundings and convenient location. Surrounded by trees and fresh Maine air, the apartment feels tucked away while remaining minutes from downtown Brunswick, Freeport outlets, coastal walks, and seasonal outdoor activities.

Value · Family · Condition

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!

Location · Family · Bathroom

1BR cozy, luxurious getaway @ Krista's Guesthouse

Newly built guesthouse above owner's garage with insane sunrises & great view. Property is located on 36 acres, owner lives on site in a separate house with her 3 dogs, 1 exceptionally lazy cat and 4 rogue chickens (they may all come visit you!). Grounds have ancient apple trees, loads of perennial gardens with more in progress, berries and an organic vegetable garden that we would love to share from if desired. Please do not hesitate to ask any questions! We hope to meet you soon!

Location · Family · Outdoor spaces

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!

Location · Family · Getting around

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.

Family · Location · Parking

Private Bungalow w/ Hot Tub, Free Parking & Pool

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

Family · Value · Check-in

Private apart with luxury view, mins to everything

Welcome to the Peak View Apartment! This lovely and stylish place is perfect for a honeymoon, anniversary or romantic getaway or for those who crave for retreat. This is what you imagine when you want to relax in the house in the mountains!!! But also great for a small family with kids! Sitting on the ridge of Pleasant Mountain, the place is minutes away from all the attractions and beautiful lakes. The property will give you the full vacation in the woods experience!

Value · Family · Getting around

Mountain Treehouse Guesthouse

Spacious second story post and beam room adorned with king bed, full kitchen, bath, living area, and laundry. The guest house is located on 40 acres of wilderness with mountain views, and walking trails on the property. Just two miles from Stone Mountain Arts Center, 15 minutes from Fryeburg village, and only 25 minutes to neighboring North Conway, NH. A great retreat for all seasons. TV, High-Speed Internet, AC, Heat, Ceiling Fans, New Construction.

Location · Family · View

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

Location · Family · Outdoor spaces

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.

Location · Family · Solo travel

Waterfront Sunrise Cove Cottage

Unwind with spectacular sunrises from this sunny waterfront cottage on a tidal cove in the Kennebec River! This is the perfect home base for a midcoast Maine getaway. The post-and-beam cottage has cozy furnishings and expansive views across a field, pond, and cove. Bald eagles and osprey soar overhead, sturgeon leap in the river & nights are full of stars. Owners live on property with small dog.

Family · Location · Parking

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.

Location · Value · Indoor spaces