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Urban Seaside Retreat- East End Overlook Casco Bay

A very special retreat. Elegant and cozy, two-level, private entrance, with front row view of Casco Bay islands, parks, and easy access to the best of Portland's city life. Watch the Sun and Moon rise over the islands from this Victorian stable apartment. Walk to Portland's finest cultural and culinary offerings, to the beach for kayaking, the park for tennis, enjoy shore front trails, take a ferry to the islands. Everything to enjoy the very best of Portland is right here. (Reg.#001171-2019)

Luxury Year-round Treehouse with private hot tub

The Canopy is one of 5 luxurious tiny homes that make up Littlefield Retreat, a tranquil woodland village of 3 treehouses and 2 hobbit houses – each with its own private hot tub and dock. To see all five dwellings, click on the photo to the left of “Hosted by Bryce”, then click “Show more…”. This 15-acre forest retreat on Littlefield Pond offers our guests an experience that feels like a trip up to the woods of northern Maine, but is closer to home and to all the attractions of southern Maine.

Two-Story, Direct Ocean Views on Eastern Promenade

You will be delighted by the direct ocean views in this 3-bedroom 2-bathroom apartment located on the Eastern Promenade. Cross the street to enjoy the 88-acre waterfront park for kayak rentals, a morning at the playground, tennis at the courts, a walk on the trails, an afternoon at the beach, or a picnic on the green. This two-story apartment offers a bathroom on each level, a side deck, washer/dryer for extended stay convenience, air conditioning and lots of windows to enjoy the views.

Charming, Minimal Apartment on Munjoy Hill

Located at the top of Munjoy Hill, our minimal, cozy, first floor apartment is the perfect Portland location - a short walk to numerous restaurants, coffee shops, breweries, the Old Port and Casco Bay Ferry Lines, and very close to the East Promenade with its ocean views, picnic spots, and trails for walking and running. Our place is good for couples, solo adventurers, small families, and business travelers. We live in the building and are usually around to answer question or help if needed.

Luxury One Bedroom Loft in Portland’s Old Port

Immerse yourself in the culture of the Old Port at your luxury loft. A top choice for travelers, The Docent's Collection was most recently awarded Condé Nast Readers' Choice (2025) and Tripadvisor Travelers' Choice (2025). Enjoy this spacious open-concept floor plan featuring a full-sized kitchen and bedrooms with soft luxurious linens and cozy pillows for your comfort. Admire the tapestry of a curated collection of local artists and enjoy five-star service from our local hospitality team.

Boutique 1BR Suite * East End* Bay View

Beautifully appointed boutique 1-bedroom suite in Portland’s quiet East End, featuring Maine-sourced wide-plank pine floors and seasonal Casco Bay views. Thoughtfully designed with bright modern furnishings, local artwork, Brooklinen linens and towels, and locally roasted coffee. Enjoy a comfortable queen bed, a shared patio with a grill and gas fire pit, and an easy walk to the Eastern Promenade, waterfront, and Old Port restaurants. Quiet, owner-occupied, non-smoking, no pets, no TV.

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!

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.

Adorable getaway on the Eastern Promenade

Lovely third-floor apartment on the East End just steps from the glorious Eastern Promenade. Cozy and cute, this adorable spot resides in the neighborhood which boasts the best restaurants, breweries, and coffee shops in the city all within walking distance. On a quiet residential street, there is plenty of on-street parking. This apartment is on the 3rd floor of the house . **Please note that the last 9 steps leading up to the apartment are quite steep.

Cozy Urban Treehouse on Munjoy Hill

Snack and sip your way through the food mecca that is Portland, Maine from this conveniently located, newly renovated one bedroom retreat. The lush and transportive attic apartment is easy walking distance from the Eastern Prom, the Old Port, and Bayside breweries, allowing guests a one-of-a-kind getaway. White lacquer floors are paired with antique furnishings, soft linens, and techy touches. Come for the lobster, stay for the lifestyle.

Gorgeous Studio 2 Blocks from Eastern Prom!

Located in Portland's trendy East End and within walking distance to the Old Port and Downtown, this beautiful studio is only 2 blocks from the Eastern Promenade and Casco Bay! You will have the Unit entirely to yourself with its own entrance, air conditioning, kitchenette, king sized bed and an additional pull out single. Easily walk to all of the cool breweries, great restaurants, coffee shops, and night life! Welcome to Portland!

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.