Westbrook vacation rentals

4.9 out of 5 average rating, 300 reviews

The entrance showcases large glass doors leading into a warm living area. A plush leather couch is prominently featured, with natural wood flooring visible. The staircase in the background offers access to upper levels, while a potted plant adds a touch of greenery.

Loft in Portland

Large Loft—Walk to Breweries— Coffee Bar—King Bed

Located on outer Forest Avenue in Portland, Maine, Forest Loft is an impressive, custom built, 1 bedroom / 2 bathroom apartment with vaulted ceilings and plenty of space. Due to its close proximity to the breweries on Industrial Way, Forest Loft commonly welcomes craft beer fans from all over the world. Enjoy the proximity to popular amenities while only a short ride from downtown Portland. MAINE'S TOP HOST OF 2022 https://news.airbnb.com/celebrating-our-top-new-hosts-in-each-us-state-for-2022

4.93 out of 5 average rating, 238 reviews

An indoor garage space is set up for leisure, featuring a blue ping pong table positioned centrally. A wooden cabinet and a chair are visible against the wall, with a glimpse of outdoor greenery seen through an open door.

Guest suite in Westbrook

Awesome open space in Westbrook near Portland, ME!

Welcome!! We're excited to share our house with you! You'll get the whole ground level of the house - two very large clean modern rooms with a private entrance, bathroom, and direct yard access to the hammock, fire pit, and wildlife. Off-street parking for 2 cars, kitchenette, 300Mbit wifi, smart TV, heat, ping pong, darts, and much more! 15 mins downtown Portland ($15 Uber) 1 mile from I-95 11 mins from the airport We will give you awesome tips on everything in the area and beyond!

4.97 out of 5 average rating, 216 reviews

A private outdoor sitting area features a round table surrounded by two metal chairs on a wooden deck. The space is bordered by a railing and overlooks greenery, providing a tranquil atmosphere for outdoor relaxation.

Guest suite in Back Cove

Sunflower Retreat in North Back Cove

The Sunflower Retreat is a private, self-contained, peaceful hideaway. Located in the back half of an adorable 1920's home, this BnB space has everything you could need. A driveway leads you around to the back of the house, where a stone walkway guides you to your own private patio and entrance. A comfortable queen bed, kitchenette, full bathroom, closet, dining nook, black-out curtains, eatery, and television are included. Free street parking. Located in close proximity of many things!

4.99 out of 5 average rating, 140 reviews

A gravel pathway winds around the side of the property, bordered by green grass. Colorful flowers are visible in garden beds along the path, enhancing the natural landscape. Trees are positioned in the background, providing a serene setting.

Apartment in Windham

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.

5 out of 5 average rating, 436 reviews

A charming exterior of a black post and beam barn is displayed featuring a natural wood door with metal hardware. A decorative star adorns the upper section of the barn, while a small metal bench sits on a gravel pathway beside the structure.

Barn in Stroudwater

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.

4.96 out of 5 average rating, 482 reviews

The cozy cabin is illuminated by soft outdoor lights, enhancing its charming facade. The front porch features a seating area, with potted flowers adding a touch of nature. The surrounding grassy area includes stone steps leading towards the entrance, promoting a welcoming atmosphere.

Tiny home in Portland

The Garden Cabin Tiny Home

Curious about tiny homes? Love dogs, gardens, pine trees, campfires, and birds? Hate cleaning fees? Our private 128 sqft cozy cabin is for you! On the spectrum between camping and a hotel room, it's a chill place to call home while visiting Portland. Enjoy our garden while sipping a beverage from your own deck or around the campfire. Heat and A/C when needed. Please, no smokers, kids under 13, or guest pets. STHR-000718-2018

4.99 out of 5 average rating, 260 reviews

A cozy living area is showcased, featuring a light grey sofa and a patterned armchair. A glass coffee table rests in the center, surrounded by natural light. Kitchen space is visible in the background, complemented by wooden accents and white cabinetry.

Guesthouse in Windham

Cottage on Black Brook Preserve

This charming cottage is thoughtfully furnished, it's your home away from home! Clean and cozy, one bedroom with queen size bed and full kitchen. Sit in front of the gas fireplace or on your own private deck overlooking the 105 acres of Black Brook Preserve. Take a hike, snowshoe or cross-country ski right outside your door. We now have new sofa, bed, refrigerator, stove, as well as shower and bathroom flooring.

Apartment in Cumberland Mills

A wall-mounted artwork features an abstract design with two cats and a plant, set above a black storage shelf. Three large white bottles labeled "Body Wash," "Shampoo," and "Conditioner" are displayed symmetrically on the shelf, providing essential toiletries.

4.9 out of 5 average rating, 199 reviews

Cozy 2 BR Apt in Walking Distance to Restaurants

This is a private 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.)

4.9 out of 5 average rating, 551 reviews

Home in Westbrook

Reno Barn w/ a lot of Charm! Breweries & Airport

** Cozy Renovated Barn w/ artist loft ** Minutes from airport and within walking distance to the Allagash Brewing Company & other breweries. Lots of hiking trails along the Presumpscot River. Short drive to downtown Portland, restaurants, music venues, beaches, lighthouses and nightlife. Barn is located in a quiet area ~ relax on the back deck with a glass of wine star gazing. Come check us out!!

4.92 out of 5 average rating, 188 reviews

A serene lakeside view features a calm water surface reflecting the surrounding greenery. Several chairs are arranged near the water's edge on a wooden deck, complemented by a sandy beach area. A dog can be seen walking along the shoreline, adding a lively touch to the tranquil scene.

Guest suite in Windham

Millers Private Studio on Highland Lake

If you're looking for a quiet, cozy getaway with private Highland Lake access this is the place for you. Private deck to enjoy your morning coffee, close to everything but in a country setting. 15 minutes from 95, Portland ME and Sebago Lake Region. Small boat launch available, Swimming & Fishing . Large back yard and a great window view of the lake. Wifi 100(mbps) for a work from home atmosphere.

4.96 out of 5 average rating, 230 reviews

A light-filled studio interior showcases a sitting area with a patterned sofa and wooden chairs, complemented by a dresser and small table. A fully equipped kitchen is visible, featuring a refrigerator and minimalist decor. Natural light enters through two windows, creating a serene ambiance.

Guesthouse in Cumberland

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.

4.94 out of 5 average rating, 133 reviews

A bright kitchen countertop features a glass jar filled with assorted coffee pods and a small white bowl. A Keurig coffee maker is positioned beside the jar, with white subway tiles providing a classic backdrop. Electrical outlets are visible on the wall.

Apartment in Westbrook

Peaceful 1BR | Reading Nook | Near Portland

This bright and charming second-floor apartment is part of a beautifully renovated 1890s home in the heart of Westbrook. Just a short drive from the excitement of Portland, it’s the perfect blend of quiet comfort and city convenience. Explore nearby local shops, cafes, and riverfront trails, or head into Portland for world-class dining, galleries, and entertainment.

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Popular amenities for Westbrook vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in Westbrook

5 out of 5 average rating, 4 reviews

A dining table is set with two dark mugs and matching placemats, accompanied by utensils. A decorative vase with floral accents adds a touch of color. Sunlight illuminates the space, highlighting the surrounding windows and greenery visible outside.

Apartment in Westbrook

20 Min 2 Portland | Deck, Grill & Firepit | DogsOK

4.88 out of 5 average rating, 92 reviews

A welcoming living space is shown, featuring a contemporary kitchen with white cabinetry and a dining area with seating for six. A comfortable pink chair and a black coffee table sit atop a patterned rug. Bunk beds are visible in the background, providing additional sleeping arrangements.

Apartment in Falmouth

Peaceful & Cozy Falmouth Getaway

5 out of 5 average rating, 17 reviews

The exterior of the property is presented, featuring a charming two-story house with a peaked roof and wooden double doors. Large windows enhance the facade, surrounded by manicured grass and vibrant flower pots. A stone pathway leads to the entrance, framed by lush greenery.

Barn in Scarborough

Stunning 1 bedroom barn.

4.96 out of 5 average rating, 24 reviews

Apartment in Westbrook

Suburban Studio Apt in a quiet family neighborhood

Place to stay in Westbrook

4.76 out of 5 average rating, 59 reviews

Serenity between the lakes & sea

4.82 out of 5 average rating, 92 reviews

A spacious living area is furnished with a large, dark fabric sectional sofa adorned with decorative pillows. A simple black coffee table is positioned at the center, featuring a small decorative arrangement. Light gray walls enhance the modern design, and closet doors are visible in the background.

Guesthouse in Westbrook

Modern stay Westbrook Maine

4.89 out of 5 average rating, 76 reviews

A compact bathroom features pastel green and white tiles. A single sink with a mirrored cabinet above is located beside a toilet. Soft lighting is provided by wall-mounted fixtures. Fresh towels are neatly displayed, and a decorative storage box sits on the counter.

Home in Westbrook

Quaint farmhouse master suite w/private bath