Holiday houses in Portland

Retro, in-town Apt-walk to old port, waterfront

Spacious, vintage 1 bedroom apartment w/living room, eat-in kitchen and bath, in ideal location-walk to all downtown dining, old port shopping, waterfront, ferry. West end, beautiful, historic neighborhood-watch exquisite sunsets at the western promenade. 2nd floor apartment in a 3 unit Victorian building on dead end, quiet, street , blocks from downtown. Queen size bed, full kitchen, bath, living room. Street parking is easy to come by. Note, steep flight of steps, no tv License#STHR0011152019

West End Artist's Getaway

Listed as one of the best Airbnb’s in Portland by Condé Nast, this wonderful artist's West End private suite is within walking distance of downtown, the best coffee shops, and dozens of restaurants. Filled with light and personal touches, this suite offers a private entrance, eat-in fully stocked kitchen, a large and sunny bedroom, and a full bathroom with antique claw foot tub perfect for a relaxing soak. A whole house water filter makes tap and shower water pure. License # STHR-003865-2021

First Floor Portland Condo 3 Bed 2 Bath + Parking

A cozy getaway nestled in the Portland's Deering neighborhood. Enjoy the retreat that this beautiful light-filled condo has to offer, whilst being less than three miles from the Old Port! The space is bright, and open--filled with luxurious touches and local Maine art. With three bedrooms and two full bathrooms, there is plenty of space for a large group to stay. Also, enjoy three free parking spots during your stay. We can't wait to have you! 3.5 miles to Airport 3 miles to bus station

Captain’s Quarters | West End • Patio • Parking

Welcome to Captain’s Quarters! Experience Portland's historic West End in this nautical-chic apartment. Great space for a weekend getaway or extended work-from-wherever stay. 🛏️ Studio apartment, queen bed 📍 Central peninsula, historic West End 🚘 Parking (off-street) 🍴 Full Kitchen 🔥 Courtyard 🏠 2nd-floor unit 💻 WiFi (1 GB) 📺 TV 👩‍🍳 Steps from Tandem, State Theatre, Chaval & more 🦞 Short walk to Downtown, Arts District, Old Port & East End ⛱️ Quick drive to several beaches

The Maine Frame | Modern A-Frame Cabin in Freeport

• Perfect for small families or couples, our signature A-Frame cabin features a modern interior gas burning fireplace, soaring ceilings, huge windows, stylish interiors, and all the comforts of home. • This cozy 1,100 square foot space comfortably accommodates up to four guests in two bedrooms (one with a King-size bed and the other with a Queen-size bed) and a shared bathroom. • 7 minute drive to downtown Freeport. • Proud to be ranked in the top 1% and voted Guest Favorite!

Mary J. Eastburn House – Eastburn Suite

City of Portland Reg. No. : STHR-002888-2021 Perched on a quiet street corner on Portland's Western Promenade, this historic residence enjoys what Longfellow called the "rarefied air of this little town by the sea," spectacular sunsets, and commanding views of the White Mountains. Built in 1891, the Mary J. Eastburn House now offers 3 private and exclusive guest suites for those who enjoy the grandeur of the past, updated with the luxuries and technology of the present.

Old Port Penthouse Suite - Amazing Harbor Views

CO2024-01992 Private Old Port Penthouse w/Breathtaking Views + Your Own Cupola. Quiet + Secure. Gorgeous contemporary suite full of light located right across from the working waterfront. Lobster and seafood off the boat is 100 meters from your front door. Watch the ferries to the islands from the cupola. Smell the salt air from your private deck. Welcome to Portland! Please note: animals (including assistance animals) not allowed due to owner's health.

Walk-able Portland Studio

NEWLY RENOVATED! Cozy studio apartment in a historic building, located in Portland's East End Neighborhood. This location can't be beat! The Space features original hardwood floors, and large windows, subway tiled shower and thoughtful decor. Portland Food Co-Op, Lookin Good Laundromat, and Walgreen's are steps away. Walking distance to Eventide, Honey Paw, Duck Fat, LB Kitchen, Washington Ave Breweries and Distilleries and Old Port shopping district.

Downtown Historical Victorian 2 BR APT

The West End is one of Portland's most historical districts. The house is within walking distance of Long Fellow Square, and the Western Promenade. It is a great home base while exploring. From its rich history rooted in the Victorian era, to its parks and restaurants, Portland's West End is consistently ranked as a favorite local hotspot. New reno located on a popular street in a neighborhood filled with historic homes.

Beautiful West End studio, hot tub, free parking

Charming, comfortable, well-appointed studio, in an historic building, just steps away from everything downtown Portland has to offer: restaurants, museums, shopping, galleries, parks, Congress Street, and the Old Port. Close to Maine Medical and Mercy Hospital, the Portland Expo, Sea Dogs stadium, and Deering Oaks Park. The studio rental includes free parking for one car and exclusive use of a hot tub.

Cozy Rock Cabin #thewaylifeshouldbe

*As seen on Magnolia Network's 'The Cabin Chronicles'* Cozy Rock Cabin is an 800 sq ft cabin on three acres of wooded land. Carefully designed for couples and digital nomads, it has everything you'll need to explore southern Maine (#thewaylifeshouldbe) or just stay cozy in front of a fire. Follow the journey on IG at @cozyrockcabin!

Self-check-in | Desk | Washer + Dryer | Kitchen 2

This prime space is located a block from Deering Oaks Park, just down the street from Maine Medical Center, the Western Promenade, close to many restaurants, bars & cafes in the neighborhood. Since the apartment is located in the heart of Portland, you can expect typical city noise from pedestrians, cars, and emergency vehicles.