Vacation rentals in Westbrook

Cozy Cottage Retreat near Breweries & Airport

Cozy Cottage Retreat w/ Loft near Portland Welcome to your Maine escape. Reno barn offers a warm, cottage-inspired atmosphere with character, an open loft, and inviting spaces for rest and connection. Located mins from the airport and within walking distance to Allagash Brewing Company and other local favorites. A quick drive to downtown Portland, beaches, lighthouses, and live music. End your evenings on the private back deck — wine in hand, stars overhead, and nothing but quiet around you.

Cozy Tiny Home | Fireplace • 9 Miles to Portland

This unique cottage has a style all its own. Discover modern comfort in our brand-new suburban tiny home located in The Downs in Scarborough, ME! This stylish space offers all-new amenities and a cozy atmosphere. Ideal for solo travelers or couples, but can accommodate up to four guests. Enjoy a private escape while being ~9 miles from Portland and ~6 miles from the beach. Experience efficient living without compromising on luxury. Book now for a fresh, contemporary getaway!

The Roost - lovely one bedroom efficiency unit

Staying at the Roost means you will be 15 minutes to the ocean, the airport and to the Old Port; 10 minutes to nearby lakes and rivers; 5 minutes to everything downtown Westbrook has to offer, including many restaurants, parks, live music venues, shopping and a movie theater: what you are looking for is nearby! Kick back and relax in this calm, stylish space with a queen-sized bed, kitchenette, dining/work area, excellent wifi, a full bathroom and a big yard.

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.

Portland Back Cove Hideaway-1 BR- With Patio

Our quiet residential Back Cove neighborhood is your perfect retreat from a busy day exploring Portland. Take a short drive to the center of the city, or enjoy the waterfront walking and biking trail which loops around the cove. Dine at Tipo or Woodford F&B, two neighborhood favorites. Come home to this newly renovated space and relax on the patio! Our space can accommodate four guests. Great for a family, or close friends! We look forward to hosting you!

Beachy 1BR Atop Munjoy Hill+Steps to Eastern Prom

Beach vibes in this cozy space make for a comfortable home base while you explore Portland's Munjoy Hill neighborhood. The apartment is situated in the East End, a short walk to the Eastern Promenade, local grocery, great restaurants and bakeries. Head to the East End Beach, or paddle to the islands in Casco Bay. Walk to the Old Port from this quiet neighborhood in 15 minutes or head over to Washington Ave, for amazing food, distilleries and breweries!

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.

Central-Local Studio in Vibrant Portland, Maine!

Spacious and private studio apartment, with sitting area, queen size bed, table and chairs for dinning, kitchen and full bathroom. Newly updated appliances in a well maintained building. Wood floors lend charm, while modern decor makes for a contemporary feel. This comfortable space is perfect to come back to after exploring the surrounding neighborhood. The Studio is steps away from Portland's best restaurants, shops, nightlife and more!

Old Port on foot

Newly renovated, spacious and modern top-floor condo in a posh historic building in the heart of downtown Portland. Leave your car behind! Walking distance to tons of bars/restaurants, stores, a block from the Portland Harbor/Commercial St and 3 blocks from Merrill Auditorium. Please note there is an additional $50 cleaning charge for stays greater than 7 nights. For stays greater than 14 nights, the cleaning fee is $180.

Oceanside Modern Victorian 2BR- East End/ Downtown

Classic New England style home, recently renovated and updated with modern amenities. A stone's throw from Portland's best public park, The Eastern Promenade. The Promenade boasts beautiful ocean views, a public beach, basketball & tennis courts & large playground. The neighborhood offers great restaurants and coffee shops. The Old Port and the rest of Downtown Portland is a 10 minute walk or 4 minute Uber ride away.

Cozy 2 Bedroom Apartment Close to Portland

This is a newly renovated two bedroom apartment in a great location (15 minutes to downtown Portland). The apartment is in walking distance to eateries, Riverbank Park, grocery stores and local breweries. It is also located across the street from the police station on a dead end street. The unit is child friendly and has a Pack 'n Play and high chair. (Please note that linens are not provided for the Pack n’ Play.)

Cottage Under a Crabapple Tree

Steps from extensive nature trails and wildflower meadows, this quaint studio cottage is nestled conveniently between the restaurants and breweries of Portland, the outlet shopping of Freeport, and miles and miles of rocky coastline. Perfect for a quiet Maine getaway, lodging near Cumberland fairgrounds and other local attractions, or a visit to family and friends in the area.