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.

%{current} / %{total}1 / 1
Guest favourite
The cabin's exterior is captured through a flickering flame, showcasing large glass windows that invite natural light. Surrounded by lush trees, the cozy structure features a modern design, blending seamlessly with the serene outdoors.
Home in Naples
4.99 out of 5 average rating, 170 reviews

LUX Designer Private Waterfront Hot Tub - Secluded

Waterfront GLASS cabin with privacy professionally designed, escape to somewhere really special. Crooked river acres surrounding the house with the river wrapping around the property. Dock with direct access to Sebago lake and state park just minutes away, Outdoor shower, hot tub, hammocks, BIG walk-in shower w/ window. Heated bath floors, ac. See through Fireplace. The property has its own sandy swimming beach, pets are welcome. Come enjoy privacy and the space to run around seconds to Sebago.

Guest favourite
A charming coastal home is showcased with light-colored siding and a bright blue front door. Surrounding greenery includes tall trees and manicured shrubs. The property is set back from a grassy area, adding to its inviting curb appeal.
Home in Falmouth
4.9 out of 5 average rating, 298 reviews

Amazing Bay View Home with Hot Tub

This enchanting 2-bedroom home is a coastal dream come true! Luxurious and well-appointed, Casco Bay House sleeps up to six, provides a five-star stay, offers all of the comforts of home AND a relaxing hot tub spa. With stunning views of the water, the house also has easy access to dining, shopping, and sightseeing in Portland's lively Old Port district (just 5 minutes away). Whether you seek quiet tranquility or want to hit the town, this waterside house is the perfect home away from home!

Guest favourite
Home in Westbrook
4.89 out of 5 average rating, 600 reviews

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.

Guest favourite
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
4.89 out of 5 average rating, 347 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 favourite
The exterior of a post and beam cottage is shown, featuring a light wood facade and a brown shingled upper section. Two black Adirondack chairs are placed on a wooden deck, accompanied by potted plants. Large windows offer a view of the forested surroundings under a partly cloudy sky.
Cottage in Pownal
4.99 out of 5 average rating, 448 reviews

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.

Top guest favourite
A charming house exterior is framed by lush greenery and blooming pink flowers. The welcoming front porch features a white railing, while multiple windows showcase warm lighting from inside, suggesting a cozy and inviting atmosphere.
Home in Westbrook
4.99 out of 5 average rating, 107 reviews

Huge 7 bedroom Farmhouse close to Portland

Great room , fully equipped kitchen, 3 separate suites with bathroom and a combinations of beds from California King to bunk bed. Yellow Suite sleeps 5 with kitchenette, TV lounge/office 1st floor Blue suite sleeps 5. Orange suite sleeps 10. Each room has its own AC. Great room combines Kitchen and Parlor with TV and couches, Patio with grill and fire table. Free parking for 8 cars. Walk to Restaurants(see pictures) Uber to Old Port. No checkout duties. Ask about midweek extension.

Top guest favourite
The exterior of the A-frame cabin is showcased, featuring a unique wooden facade and metal roof. Sunlight streams through tall triangular windows, illuminating the surrounding wooded area. A gravel path leads to the entryway, enhancing the cabin's connection to nature.
Cabin in Freeport
5 out of 5 average rating, 105 reviews

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!

Superhost
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
4.82 out of 5 average rating, 110 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 favourite
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
4.98 out of 5 average rating, 176 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 favourite
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, 468 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 favourite
The image features a studio layout with four sections. A cozy sitting area includes a blue sofa and armchair, facing a smart TV. A table set for dining is seen next to a modern kitchen. A spacious king bed is presented with decorative pillows, and a coffee table adorned with tasteful decor completes the scene.
Apartment in Westbrook
4.93 out of 5 average rating, 122 reviews

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.

Guest favourite
Apartment in Cumberland Mills
4.91 out of 5 average rating, 101 reviews

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.)

Popular amenities for Westbrook vacation rentals

When is the best time to visit Westbrook?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$170 CAD$160 CAD$157 CAD$178 CAD$193 CAD$206 CAD$231 CAD$231 CAD$197 CAD$216 CAD$199 CAD$209 CAD
Avg. temp-4 °C-3 °C1 °C7 °C13 °C18 °C21 °C21 °C16 °C10 °C4 °C-1 °C

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 370 vacation rentals in Cumberland Mills, and over 400 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.

  • Are there family-friendly vacation rentals in Westbrook?

    Westbrook has more than 40 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Westbrook?

    Experience the best of Westbrook with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • 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 apartment rentals in Westbrook have wifi?

    Absolutely! We offer over 20 apartment rentals with wifi in Westbrook. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Westbrook have a bbq area?

    Absolutely! We offer over 10 house rentals with a bbq area in Westbrook. Enjoy a tailored experience with all the comforts you desire.

Quick stats about vacation rentals in Westbrook

  • Total vacation rentals

    Explore 100 vacation rentals in Westbrook

  • Nightly prices starting at

    Westbrook vacation rentals start at $54 CAD per night before taxes and fees

  • Verified guest reviews

    Over 6,630 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wifi availability

    100 of Westbrook vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill, and Laptop-friendly workspace across Westbrook rentals

  • 4.8 Average rating

    Westbrook stays are highly rated by guests—averaging 4.8 out of 5!

  1. Airbnb
  2. United States
  3. Maine
  4. Cumberland County
  5. Westbrook