Where should I stay in Westbrook?

Make yourself at home in Westbrook by choosing from our most frequently booked neighborhoods. We have over 400 vacation rentals in Nasons Corner, over 520 vacation rentals in Stroudwater, and over 390 vacation rentals in Riverton.

Are there pet-friendly vacation rentals in Westbrook?

Four-legged friends are welcome in Westbrook. Choose from more than 30 vacation rentals for guests traveling with pets.

Are there vacation rentals with a dedicated workspace in Westbrook?

Yes! Work meets play with ease at over 50 vacation rentals in Westbrook featuring dedicated workspaces. Stay connected and productive in your home away from home.

How much does it cost to stay in apartment rentals in Westbrook?

Experience the best of Westbrook with our apartment rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Are there family-friendly house rentals in Westbrook?

Westbrook has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Do house rentals in Westbrook have air conditioning?

Absolutely! We offer over 30 house rentals with air conditioning in Westbrook. Enjoy a tailored experience with all the comforts you desire.

Do house rentals in Westbrook have wifi?

Absolutely! We offer over 40 house rentals with wifi in Westbrook. Enjoy a tailored experience with all the comforts you desire.

What are the most popular amenities for House Rentals in Westbrook?

Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with air conditioning, over 40 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Vacation rentals in Westbrook

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Westbrook

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

The spacious loft is highlighted by 16-foot ceilings and multiple skylights. A queen bed is positioned near a cozy seating area, complemented by a wooden dining table. Eye-catching artwork adorns the walls, and natural light fills the room through large windows.

Loft in Falmouth

4.95 out of 5 average rating, 646 reviews

Loft Apartment on Tree-Lined Street in Falmouth

Staying in this huge second floor loft (32'x25’), you will find a quiet oasis in the treetops. The 16' ceilings and stylish decor provide sanctuary after a busy day of sight seeing. We offer a queen bed and two twins. You are surprisingly close to Portland's restaurants and shops, well located for day trips up and down the Maine coast. Start the day with a self-brewed local coffee. Relax at the end of the day streaming your favorite entertainment on a 55" 4K-HD TV paired with a Sony sound bar. Soak in the secluded backyard HOT TUB, OPEN YEAR ROUND, with a pool available in the summer. The loft is bright and airy given its 16 foot cathedral ceilings, four sky lights and five large windows. Each window has room darkening blinds and full curtains that can darken the room for an afternoon nap. It is accessed through a private entrance up a wide stairwell in the stand alone garage. An In-Suite thermostat allows you to control a comfortable room temperature. The newly renovated space is equipped with queen bed and a twin trundle bed, which pulls out a second twin bed (sleeps two). The beds are fitted with 100% cotton sheets. The living room lounge area has a 55" 4K Ultra UHD flat screen TV equipped with a Roku streaming device. Spectrum TV streaming app provides the broadcast networks, as well as ESPN, TNT, AMC, Bravo and others. Bring your log-in ID to access your favorites programming, such as NETFLIX, HBO-Go, HULU and SlingTV. A Blu-ray/DVD player is available upon request. (There are 3 redbox locations within 2 miles.) The full bath has a shower stall (no tub). Plush towels and premium soap, shampoo and conditioner are provided. Enjoy use of backyard hot tub year round and in ground pool during summer season. Children are welcome. The loft is stocked with books and board games. There is a baby gate available. We are happy to assist you in making plans to see the area. Please ask us if you need recommendations to things to do during your stay. While you will have your own private space and free standing four walls, we will generally be nearby and available. The setting of this property is a long and winding street with large, open lots and eye-catching homes. Stroll to the mouth of the Presumpscot River, which empties into Casco Bay. Dine and shop in the heart of the Old Port, only 14 minutes away. There are no bus lines close to the house. One could manage navigating the area via Uber if not driving a car. The loft has an efficiency kitchen with toaster oven, mini fridge, coffee maker, electric tea kettle, two burner hot-plate, pans, utensils, plates and silverware. We keep the loft stocked with Wicked Joe Sumatra blend. Wicked Joe is a local family-owned company committed to producing exceptional coffees using sustainable business practices from crop to cup. Additional large beach towels provided for hot tub and pool use. We can connect you with local area shops for surf board, stand-up paddle board and bike rentals. We have plenty of ideas on restaurants, shops and points of interest which we are happy to share. Local area magazines and tourist information available in the loft.

Superhost

A spacious dining area is highlighted by a wooden table surrounded by white chairs. A staircase with wooden railings leads to the upper level. Natural light fills the room through multiple windows, enhancing the warm wooden details of the walls and floor.

Loft in Portland

4.9 out of 5 average rating, 319 reviews

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

Top guest favorite

A spacious yard features a hammock set up for relaxation, accompanied by a fire pit area. The light yellow house stands in the background, offering multiple levels and direct access to outdoor spaces. Lush greenery surrounds the property, contributing to a serene outdoor setting.

Guest suite in Westbrook

4.93 out of 5 average rating, 248 reviews

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, fast wifi, smart TV, heat or A/C, and much more! We will give you awesome tips on everything in the area and beyond! 15 mins downtown Portland (Uber/Lyft available) 1 mile from I-95 11 mins from the airport

Top guest favorite

A wooden deck leads to the entrance of the yurt, featuring two green Adirondack chairs flanking the doors. The surroundings are wooded, with a carpet of forest floor visible and trees providing a natural backdrop.

Yurt in Chebeague Island

4.98 out of 5 average rating, 165 reviews

Yurt on Chebeague Island

Imagine staying in a yurt in the woods of Chebeague Island, nestled peacefully in a private clearing in the woods. Explore island beaches and hidden trails. This yurt is “glampy” inside with leather chairs and a substantial log bed. The yurt has a rusticator kitchen with all of the basics for cooking, small fridge, stovetop, sink. Water. Outdoor fire pit. WiFi . Check ferry options on Casco Bay Lines or Chebeague Transportation. Host will provide transport to/from ferry to the yurt.

Guest favorite

A spacious living area features a sectional sofa in soft brown upholstery, accented with decorative pillows. A black coffee table displays a decorative centerpiece, while a floor lamp adds light. The room is complemented by light grey walls and modern decor.

Guesthouse in Westbrook

4.83 out of 5 average rating, 101 reviews

Modern stay Westbrook Maine

Welcome to our modern 1-bedroom basement retreat, nestled in the charming town of Westbrook, just a short 3-minute drive from the Portland, Maine. With its stylish design and upscale amenities, this Airbnb offers the perfect blend of comfort and convenience for your stay in the area. The bedroom features a Queen-size bed, a queen-size pull-out sofa in the living area, accommodating additional guests comfortably in the spacious living area. There’s a $200 pet fee per pet.

Top guest favorite

A compact sleeping area features a queen-sized bed with a decorative white throw. Flanking the bed are two bedside tables, each topped with a lamp. Neutral-colored walls and soft lighting create a calm and inviting ambiance.

Apartment in Windham

4.99 out of 5 average rating, 161 reviews

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.

Top guest favorite

A spacious sleeping area features natural wood paneling and a high ceiling. A comfortable bed is dressed in light blue and white linens, accompanied by two decorative pillows. A wooden cabinet and a bedside lamp add functional elements, while a window allows soft light to fill the room.

Barn in Stroudwater

5 out of 5 average rating, 458 reviews

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.

Top guest favorite

The interior of the yurt is divided into two distinct areas. One side features a spacious bed with light bedding, while the other side includes a cozy loveseat and a small coffee table. An area rug adds warmth to the flooring, enhancing the inviting space.

Yurt in Windham

4.99 out of 5 average rating, 103 reviews

Sebago Sunrise Yurt - Trail Access!

Nestled between Portland's fine dining and Sebago's outdoor fun, the Sunrise Yurt is a great camping spot to explore what Southern Maine has to offer. Park & take a short walk to the back 2 acres of my property. The yurt overlooks a meadow & faces the sunrise. Located with access to the Sebago to the Sea Trail - 28 miles of walking & biking paths. .5 mile walking distance to Presumpscot River. *Please read 'Show More' notes section for important details.

Guest favorite

A dining area features a round wooden table with black dining chairs set atop a textured area rug. The kitchen is equipped with white cabinetry, modern appliances, and a spiral staircase leading to an upper loft. Natural light enters through the window, accented by light green curtains.

Home in Westbrook

4.9 out of 5 average rating, 572 reviews

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!!

Top guest favorite

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

4.92 out of 5 average rating, 199 reviews

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.

Top guest favorite

A spacious bedroom features a king bed adorned with striped bedding and decorative pillows. A wooden nightstand with a lamp is positioned beside the bed. Natural light filters through the window, illuminating the subtle wall hues and the soft texture of the area rug.

Apartment in Cumberland Mills

4.89 out of 5 average rating, 217 reviews

Cozy one bedroom on 2nd floor, close to Portland

Minimalist, boho vibe set in a vintage back drop. The trim, moldings and radiators are original to our 1890 home but with clean design you won't feel the clutter of vintage. Guests looking for a quiet retreat or calm vacation spot will enjoy. 15 minutes to Portland. 30 to LL Bean and Freeport for great shopping. Netflix etc in the room.

Guest favorite

The modern kitchen features a spacious wooden island with seating for four. Stainless steel appliances, including a refrigerator and gas range, are complemented by white cabinetry. A window provides natural light, illuminating the clean and inviting workspace.

Apartment in Falmouth

4.87 out of 5 average rating, 109 reviews

Peaceful & Cozy Falmouth Getaway

Relax with the whole family at this peaceful home away from home. Enjoy our brand new one bedroom apartment above a detached garage. There is a convenient private key coded entrance. We are located in West Falmouth situated about 5 miles from downtown Portland, a great home base for exploring Maine's towns, beaches, mountains and more!

Vacation rentals for every style

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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

Top guest favorite

The living room features two brown leather sofas and a round coffee table placed on a soft area rug. A wall-mounted TV displays a scenic view, while the blue walls and large windows enhance the bright and airy ambiance. Two accent chairs offer additional seating.

Apartment in Westbrook

5 out of 5 average rating, 11 reviews

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

Guest favorite

A bright hallway features wooden flooring and natural light filtering through large windows. Exposed wooden beams and a brick wall add character. A cozy seating area with red sofas is visible at the end, alongside a modern kitchen space. A bathroom door is located to the left.

Apartment in Downtown Portland

4.94 out of 5 average rating, 702 reviews

Extraordinary Architectural Masterpiece Downtown

Guest favorite

The exterior of a historic Victorian mansion is showcased, featuring a spacious lawn and lush greenery. The house includes detailed architectural elements with gables and a prominent chimney. A wrap-around porch provides access to multiple entry points that resonate with the home’s original character.

Home in Westbrook

4.93 out of 5 average rating, 153 reviews

Westbrook Estate - 10 Minutes to Portland

Guest favorite

The exterior of the duplex is shown, framed by lush green trees and well-maintained landscaping. The structure features a sloped roof and a garage, with soft natural light illuminating the grassy front yard. A quiet residential street runs in front, emphasizing the serene setting.

Place to stay in Westbrook

4.79 out of 5 average rating, 70 reviews

Serenity between the lakes & sea

Guest favorite

An outdoor patio area is featured, bordered by wooden railings, with a hammock and a tall table surrounded by matching chairs. The space is set against a backdrop of greenery, creating an inviting atmosphere for relaxation.

Guesthouse in Cumberland Mills

4.98 out of 5 average rating, 48 reviews

Riverfront guest house w/ patio

Top guest favorite

The treehouse, shaped like a fox, is elevated among the trees with large windows that allow natural light to flood the interior. Its unique architecture features a copper roof and warm illumination, creating a welcoming appearance against the tranquil forest backdrop.

Treehouse in Pownal

4.98 out of 5 average rating, 133 reviews

The Copper Fox Treehouse

Guest favorite

An entryway features a red door, two clocks on the walls, and a small bar table with two stools. A mirror is mounted above the table, and the space is complemented by wood accents and light-colored flooring leading to the kitchenette.

Cottage in Portland

4.9 out of 5 average rating, 583 reviews

Cozy & Quiet Modern Cottage

Guest favorite

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

4.95 out of 5 average rating, 248 reviews

Cottage Under a Crabapple Tree

Quick stats about vacation rentals in Westbrook

Total rentals
100 properties
Nightly prices starting at
$40 before taxes and fees
Total number of reviews
6.2K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
50 properties have a dedicated workspace

Frequently Asked Questions

Where should I stay in Westbrook?
Make yourself at home in Westbrook by choosing from our most frequently booked neighborhoods. We have over 400 vacation rentals in Nasons Corner, over 520 vacation rentals in Stroudwater, and over 390 vacation rentals in Riverton.
Are there pet-friendly vacation rentals in Westbrook?
Four-legged friends are welcome in Westbrook. Choose from more than 30 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Westbrook?
Yes! Work meets play with ease at over 50 vacation rentals in Westbrook featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in apartment rentals in Westbrook?
Experience the best of Westbrook with our apartment rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly house rentals in Westbrook?
Westbrook has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Westbrook have air conditioning?
Absolutely! We offer over 30 house rentals with air conditioning in Westbrook. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Westbrook have wifi?
Absolutely! We offer over 40 house rentals with wifi in Westbrook. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Westbrook?
Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with air conditioning, over 40 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Vacation rentals in Westbrook

Top-rated vacation rentals in Westbrook

Vacation rentals for every style

Popular amenities for Westbrook vacation rentals

Other great vacation rentals in Westbrook

Quick stats about vacation rentals in Westbrook

Total rentals

Nightly prices starting at

Total number of reviews

Family-friendly rentals

Pet-friendly rentals

Rentals with dedicated workspaces

Frequently Asked Questions

Destinations to explore