Apartment vacation rentals in Cumberland

Thompson's Point Studio

Our charming studio apartment in the Libbytown neighborhood is walking distance to Thompson's Point & Amtrak (15 minutes!) and the trendy West End, while still being quiet and secluded. Enjoy a concert or Portland's famous restaurant scene and come home to a memory foam bed and all the little essentials like a white noise machine and a bar kit for homemade cocktails. We have been hosts for 8 years near Acadia National Park and are so excited to share our new home of Portland with guests as well!

Apt in Victorian Mansion w/ Hot Tub, Parking, Pool

Contemporary styling with old-world charm, the Apartment in the Leonard Bond Chapman House offers a relaxing stay only 10 min to downtown. Whether you plan to soak in the shared hot tub, cool down in our seasonal pool, or relax by one of our fire pits, our half-acre yard offers a tranquil stay. The apartment boasts a newly renovated bathroom, radiant heated floors in both kitchen & bath, and a chef's kitchen. This grand apartment won't disappoint. L2 EV charging outlet on site #allarewelcome

Falmouth Waterfront Carriage House Apt

Waterviews! This 1 bedroom apt has a new “purple”mattress, above our detached garage in classic Maine waterfront neighborhood. Next door to the iconic Town Landing Market and Town Landing pier/beach. In beautiful Falmouth Foreside neighborhood. Walkable to Dockside Restaurant and marina, and 10 minute drive or bus to downtown Portland. 20 minute drive to Freeport shopping. We only accept well- behaved and house- trained dogs, no other pets are allowed for a fee of $75.00 per dog per stay.

Sweet 1-Bedroom Apartment in Vintage Village Cape

Built roughly 200 years ago, the traditional cape housing this first-floor apartment is located on a hilltop above the Royal River, just steps from restaurants, trails, and waterfront. It's been thoroughly renovated, and features pretty much all the comforts of home—including a full kitchen with dishwasher, a wood-burning fireplace insert, an all-natural mattress (super comfy), and a clawfoot tub-equipped bathroom. Oh, and if you're bringing a third, let me know—and I'll roll in the rollaway.

Welcome to our BoHo Treehouse! Beaches/Portland

Take it easy at this unique and tranquil getaway. This is a cute apartment with plants that makes you feel like you are in the forest. Enjoy your own private one bedroom, one bath, with a private deck. Free off street parking. Located in Saco within walking distance of downtown. 7 min drive to Old Orchard Beach. We decorated with a Bohemian Treehouse style. Perfect size for a single person or couple. We brought some of our most cherished art and plants from our own home. Enjoy!

Minutes to Portland | Spacious | One Bedroom

Conveniently located in the charming Cumberland Mills neighborhood of Westbrook, this spacious one bedroom Victorian apartment offers easy access to Portland, the jetport, the highway, Rock Row, and other Westbrook attractions. Delicious eateries, local breweries, and Riverbank Park are within walking distance. This apartment comes fully furnished with a comfortable queen bed in the bedroom, a dedicated workspace, and a Pack n' Play (please bring your own linens).

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.

Cozy King bed apt near Portland with free parking

Enjoy a comfortable and relaxing getaway in this charming second-floor studio, owned and operated by a local family. Nestled in a quiet neighborhood, yet just minutes from Downtown Portland with easy access to I-95 and I-295, it offers the perfect mix of peace and convenience. This cozy studio features a brand-new King bed with a fresh mattress and pillows, along with a 3/4 bath—perfect for unwinding after a day of exploring the city or coast.

Parking, Close to DT, Old Port, Thompson Pt

Stylish & Convenient Spacious, comfortable and sparkling-clean apartment with historic 1800s vibe—wide pine floors and exposed chimney. Thoughtfully equipped for a hassle-free stay. Conveniently located just off 295 and Steps from Bunker Brewing, minutes to Old Port, Arts District, Thompson’s Point, and Sea Dogs games. Some traffic noise expected. Booker must be over 21 Licensed by City of Portland STR

62 Views

Registration #2018-4090. Windows w/massive views from kitchen, dining & living areas, and private roof deck. Enjoy Portland's bustling harbor over morning joe or an evening glass of wine, stroll the Eastern Promenade, walk to excellent restaurants, the Old Port. Like to cook? Fully equipped kitchen! NOTE: Please *do not book this space* if you can't honestly live by our House Rules.

Beekeeper's Cottage- Peaceful,Quiet - Ocean Front

Set on 7.5 acres of fields, woods, & gardens we are off the main road. Take a 4 minute stroll down a wooded path to our private beach on Maquoit Bay. Swim, fish, hunt for driftwood, or sit by the sea & listen to the waves. We feel this property affords a quiet and relaxing oasis.

Peaceful 1BR | Reading Nook | Near Portland

This bright second-floor apartment, located in a beautifully renovated 1890s home, offers a peaceful retreat in the heart of Westbrook. Just minutes from Portland’s dining, arts, and waterfront attractions, it’s the perfect balance of small-town charm and city convenience.