
Places to stay near Casco Bay Lines
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Top-rated holiday rentals near Casco Bay Lines
Guests agree: these stays are highly rated for location, cleanliness and more.

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.

LUX Designer Private Waterfront Hot Tub - Secluded
Escape to a luxurious, privately designed glass-walled waterfront cabin on 3+ secluded acres along the Crooked River in Naples, Maine. The river wraps around, offering total privacy, your own sandy beach, dock with direct Sebago Lake access, and state park minutes away. Unwind in the year-round hot tub, outdoor shower, hammocks, or by the see-through fireplace. Luxe bath with heated floors, huge walk-in shower w/ scenic window. AC, pets welcome. Perfect peaceful retreat—come recharge!

Renovated Exchange St. Loft w/Free Parking
This renovated loft-style condo is right in the heart of the Old Port. Located on Portland's bustling Exchange Street, the loft is central to everything the Peninsula has to offer. Elevator access will take you from the apartment to the secure lobby. From there, shops, restaurants, night life and the working waterfront are just steps outside the door. Free off street parking is available for one car a few blocks away or a convenient pay-to-park garage is located next to the building.

Sunny West End Guest Suite w/Harbor Views and Pool
Enjoy views of the working harbor from this bright, two floor guest suite in the historic West End. The space features a garden oasis and seasonal, heated saltwater pool—just a short walk from the Old Port and Arts District. The suite is attached to our home but fully private, with its own entrance. (Portland City Permit: 20185360-ST) Note: Guests agree to indemnify and hold the property owners harmless from any liability for injury or property damage.

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.

Modern Studio Loft w/ Parking in Perfect Location
This spacious and comfortable studio loft is in a historic building in the heart of Portland's Arts District, where dining, shopping, entertainment, galleries, live music and more is just steps outside your door! Located on the quieter end of Oak Street, the studio is within walking distance of everything Portland's peninsula has to offer. Free parking for one car is provided in a nearby lot. 2026 City of Portland registration STHR 000854

Coastal Penthouse - Center of Downtown Portland!
Overlooking Portland’s historic downtown rests this coastal penthouse located on the most vibrant street in the city! This one-bedroom apartment is fitted out with all of the amenities needed for a Maine vacation! Enjoy relaxing in luxury while only feet away from Portland’s most popular destinations. This penthouse is perfect for those here for business or a Maine getaway!

Cityscape Loft. Central Location
Beautiful, spacious, 1 bedroom heart of the city urban apartment featuring 12 foot ceilings, high end kitchen and bath, refinished hardwood floors in a location that is absolutely terrific. Amazing City Scape Views! This is a second floor apartment. Expect stairs. Sleeps 3 : 1 Bedroom with queen bed and there is a Futon in small auxiliary room.

Modern Condo Portland's Historic Old Port District
Enjoy a stylish experience at this centrally-located loft. A converted factory building has been transformed into this chic and modern condo. Cobblestone streets, endless incredible dining and nightlife, boutiques, shops and historic architecture. A quintessential New England seacoast town and working waterfront.

INCREDIBLE! Waterfront views. 94 walk score.
Wow! Incredible 3 bedroom, 2 bath apartment with working waterfront views. Spacious apartment nestled in Downtown, between the Old Port, Arts District and West End, just steps away from all the highlights of the peninsula. You are just steps away from everything the City has to offer. STHR-000508-2018

Chic Portland Penthouse, 2BR
Enjoy a stylish experience at this centrally-located place. We are in the middle of all the excitement in the Old Port. Ride down the elevator and just out our front door you are steps to all the best that Portland has to offer. Shops, dining and night life all conveniently at your door step.

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.
Popular amenities for holiday rentals near Casco Bay Lines
Condo rentals with Wi-Fi

Luxury Beach Front Condo! Prime Location!

Charming, newly remodeled space atop Munjoy Hill.

⭐️✨⭐️ West End Old Port CLEAN, cozy, convenient

First Floor Portland Condo 3 Bed 2 Bath + Parking

Penthouse, Walk To The Old Port & The Beach!

Walk to Top Dining • Boutique Stay • Parking

Portland 1 Bedroom Condo in the Arts District.

Direct Ocean View on the Eastern Promenade
Family-friendly house rentals

Cozy Maine Cottage • Near Jetport & Coast

East End Unit

Entire house w/king bed & parking near downtown!

An Airy Private Suite steps off Washington Ave

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

Explore Portland from a 18th-Century Victorian

Modern & Sunny East End House. Private Parking!

Romantic Mirror cabin in the woods
Apartment rentals with air conditioning

In-town Artist Loft-walk to old port, waterfront

RETRO BnB in the Heart of East End Portland

Freedom Trail Apartment

Downtown Apartment w/ Parking - Come Work or Play!

Boutique 1BR Suite * East End* Bay View

Cozy SoPo Condo

Studio Apt, 7 mins to Downtown, Parking, Café

Luxury Retreat In Back Cove | 10 Min to Downtown
Other great holiday rentals near Casco Bay Lines

Quiet Comfy Victorian Escape

The Maine Frame | Modern A-Frame Cabin in Freeport

Old Port Gem- 2 BR Loft/418 Fore St

Gorgeous Studio 2 Blocks from Eastern Prom!

Crow's Nest

Cozy Lakefront Cabin-Private Dock-Kayaks-Firepit

Old Port Loft - 301

HotTub/5min to K-port, Pet friendly, @anchorunwind
Destinations to explore
- Sebago Lake
- Ogunquit Beach
- Wells Beach
- Long Sands Beach
- Popham Beach, Phippsburg
- Willard Beach
- York Harbor Beach
- Short Sands Beach
- Scarborough Beach
- Pemaquid Beach
- Footbridge Beach
- Cape Neddick Beach
- Pemaquid Point Lighthouse
- East End Beach
- Gooch's Beach
- Coastal Maine Botanical Gardens
- King Pine Ski Area
- Popham Beach State Park
- Hills Beach
- Wolfe's Neck Woods State Park
- Crescent Beach State Park
- Pleasant Mountain Ski Area
- Fortunes Rocks Beach
- Wallis Sands Beach





