Holiday rentals in Portland

Quiet Comfy Victorian Escape

Spend your vacation, work-trip, or weekend getaway in this lovely renovated cozy 2 bedroom unit. Apartment 2 is located on the second floor of a three family house where you have access to all the modern appliances: refrigerator, W/D, microwave and TV in the living room. A brand new queen bed each bedroom, with seat in cozy seating in the living room. Located in the very central Oakdale neighborhood, this unit is steps from Deering Park, Sea Dogs stadium, USM Law School and Portland's Old Port.

Dreamy Post&Beam Hideaway Near Portland & Freeport

Escape to a dreamy timber-frame cottage tucked in Maine’s woods! Soaring beams, radiant-heated floors, a king loft bed, and a crackling fire pit await. Sip coffee on one of the two decks, hike Bradbury Mountain (3 minutes away), shop Freeport (10 minutes away), or dine in Portland (20 minutes away)—then return to your cozy hideaway under the stars. Full kitchen, vaulted ceilings, radiant heat floors, private driveway, fire pit and peaceful forest views make it the perfect year-round retreat.

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.

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 - Baxter 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.

Garrison Cove Studio

Rare, Portland waterfront studio located in the heart of the historic Stroudwater neighborhood, awaits one or two guests looking for an urban hideaway. The newly created studio occupies a 150 year old post and beam barn situated on the banks of the Stroudwater and Fore Rivers. Enjoy morning coffee on the river swing, meditate to the soothing sound of the nearby waterfall or linger over your favorite glass of wine under the splendid backyard grape arbor.

Large Sunny Apartment Near Downtown/Arts District

(License Number: STHR-007574-2026) Quiet neighborhood, quick walk to downtown Portland. Short drive to beautiful sandy beaches. Newly furnished one bedroom on *3RD FLOOR*. Spacious rooms with mansard roof ceilings. Washer and dryer. Off street parking for one car. Clean and well maintained. We happily welcome guests, but if you or someone in your group has difficulty with stairs this *3rd floor* apartment may not be the best fit for you or your group.

Downtown Penthouse Suite - Stunning Harbor Views

CO2024-01992 Private 1850's Old Port Penthouse w/Breathtaking Views and Complimentary Parking Nearby. 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 ferries and smell the salt air from your private deck. Welcome to Portland! Please note: animals (including assistance animals) not allowed due to owner's health.

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.

Sunset Suite 42

Breathtaking views, privacy, and convenient location make Sunset Suite a great place to be while visiting ME! The great room with a cathedral ceiling and skylights offers the best of natural light... day and night! The Portland skyline is all yours from your private and expansive deck as you put your feet up and reminisce about your day and plan for the next.

Charming West End Hideaway. Private Parking

Built in 1835, this historical home on the West End is just steps from the best eateries, arts and shopping the city has to offer. When you arrive, park your car in your private spot behind the house and forget about it for a while. This cozy second-floor apartment is the perfect place for a getaway!