Vacation rentals in Westbrook

Find and book unique accommodations on Airbnb

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 R 655 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 7,180 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wi-Fi availability

    100 of Westbrook vacation rentals include wi-fi 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!

Top-rated vacation rentals in Westbrook

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

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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, 702 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.

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Top guest favorite
A serene vista showcases the city skyline reflected in calm waters, framed by lush green grass and trees. The scene captures a tranquil moment, inviting viewers to appreciate the natural beauty and urban blend surrounding the space.
Home in Portland
4.92 out of 5 average rating, 305 reviews

Top Deck - Portland Property with Views!

Views, Views, Views! 2 huge decks overlooking water and city skyline. This home is adjacent to Payson’s Park – Portland’s largest park. 5-7 min ride to downtown Portland and the Old Port’s fabulous bars and restaurants. The main floor has bedroom with bath, kitchen, and living room. The upstairs has a large bedroom with bath, open room that can be used as 2nd living room or a 3rd/4th bedroom space. Sleeps 10-12. Off street parking 6-8. Large yard. Portland License #STHR-002587-2020

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Guest favorite
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, 330 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!

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Guest favorite
Home in Westbrook
4.89 out of 5 average rating, 645 reviews

Cozy Maine Cottage • Near Jetport & Coast

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.

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Top guest favorite
A welcoming living area is furnished with two dark sofas adorned with vibrant orange cushions. A rustic coffee table is centered on a colorful area rug, while large windows allow natural light to fill the space, highlighting the wall art above.
Home in Portland
4.96 out of 5 average rating, 178 reviews

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

You will be close to everything when you stay at this centrally-located place with a pool and spacious yard! Enjoy the home and it is a quick 10 minute uber to downtown Portland to the most popular shops and restaurants. This home is located perfectly to explore greater Portland from beautiful parks/trials to the shopping outlets not far away. This is a family neighborhood and out of respect for my neighbor’s, quiet hours after 10 pm. No parties. City of Portland License #: STHR-004465-2022

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Guest favorite
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, 377 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

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Guest favorite
A spacious bedroom offers a large bed with a textured white blanket. Natural light fills the room through bright windows, highlighting a decorative plant in a pot. A small table at the foot of the bed is adorned with neatly arranged towels, while light-colored wood flooring adds warmth.
Condo in Portland
4.95 out of 5 average rating, 377 reviews

First Floor Portland Condo 3 Bed 2 Bath + Parking

A cozy getaway nestled in the Portland's Deering neighborhood. Enjoy the retreat that this beautiful light-filled condo has to offer, whilst being less than three miles from the Old Port! The space is bright, and open--filled with luxurious touches and local Maine art. With three bedrooms and two full bathrooms, there is plenty of space for a large group to stay. Also, enjoy three free parking spots during your stay. We can't wait to have you! 3.5 miles to Airport 3 miles to bus station

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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
4.92 out of 5 average rating, 186 reviews

Westbrook Estate - 10 Minutes to Portland

This 1882 Victorian Mansion has been renovated with a modern kitchen, 4.5 baths, and 7 bedrooms that complement the original character of the house. It features a dining room with seating for 10+, living room with 58" TV, 3rd floor bonus living room, a sunny deck with grill and patio seating, ample yard space for games, and more. Our house is conveniently located minutes off I-95 and close to downtown restaurants and breweries, while only 10 minutes to Portland and 20 minutes to Sebago.

FamilyLocationSleep quality

Top guest favorite
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
5.0 out of 5 average rating, 155 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!

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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, 138 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.

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Guest favorite
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
4.91 out of 5 average rating, 159 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.

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Guest favorite
Apartment in Westbrook
4.91 out of 5 average rating, 126 reviews

Cozy 2 Bedroom Apartment Close to Portland

This is a newly renovated two bedroom, two story 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.)

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Popular amenities for Westbrook vacation rentals

When is the best time to visit Westbrook?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR 2,129 ZARR 2,178 ZARR 2,129 ZARR 2,129 ZARR 2,408 ZARR 2,604 ZARR 2,784 ZARR 2,784 ZARR 2,375 ZARR 2,604 ZARR 2,408 ZARR 2,522 ZAR
Avg. temp-4°C-3°C1°C7°C13°C18°C21°C21°C16°C10°C4°C-1°C

Frequently Asked Questions

  • What are the best places to stay in Westbrook?

    Vacation rentals are available throughout Westbrook, with many guests choosing homes near the river, parks, or historic downtown for ease of access to local amenities. Neighborhoods around the city are known for their welcoming feel and residential charm.

  • What are the best things to do in Westbrook with kids?

    Many families explore playgrounds, riverfront parks, and local recreation centers in Westbrook. Community pools and skating rinks are frequently suggested for active outings, and children often enjoy easy trails or attending family-oriented events at local parks.

  • What are some of the best things to do in Westbrook?

    Explore trails and riverfront parks, browse local art spaces, or catch performances at community venues in Westbrook. Many visitors enjoy discovering independent shops, sampling food at farmers markets, and experiencing local festivals throughout the year.

  • How is the weather in Westbrook?

    Westbrook has cold winters, with temperatures from 16–38°F (-9–4°C) and moderate snowfall, while summers are mild and pleasant, often reaching 74–80°F (23–26°C). Spring and autumn bring comfortable weather and frequent rainfall, so a rain jacket is useful.

  • When is the best time to visit Westbrook?

    Late spring through early autumn is often recommended for visiting Westbrook, when temperatures are milder and local events are frequent. Winters are cold, with average temperatures ranging from 16–38°F (-9–4°C), so those who enjoy snow activities have options, too.

  • What are the best places to visit in Westbrook?

    Presumpscot River Preserve, local galleries, and community parks are frequently suggested places to visit in Westbrook. The city’s historic downtown and annual community celebrations add to its inviting atmosphere.

  • What are some hiking trails in Westbrook?

    Westbrook has woodland trails, such as those in Mill Brook Preserve, where you can explore quiet forests and spot seasonal wildlife. The Presumpscot River Trail is often recommended for gentle riverside walks and birdwatching.

  • What are some family activities we can do in Westbrook?

    Families in Westbrook frequently enjoy picnics in local parks, nature walks on nearby trails, and playgrounds suited for a variety of ages. Seasonal fairs and craft events add community-focused fun throughout the year.

  • What are some of the best day trip ideas from Westbrook?

    Travelers often explore nearby beaches, classic New England lighthouses, or cultural attractions in greater Portland. Nature reserves and local farms around the region are also popular for those seeking outdoor experiences or fresh local produce.

  • Are there any pet friendly accommodations available in Westbrook?

    Some vacation rentals in Westbrook welcome pets, offering features like fenced yards or nearby access to walking trails. Hosts may have specific guidelines, so it is a good idea to check for details during booking.

  • What are some local tips for visiting Westbrook?

    Layered clothing is useful due to changing weather, and waterproof footwear is helpful for exploring trails after rain. Locals often suggest picking up fresh eats at the farmers market and joining in community gatherings for a taste of Westbrook's welcoming spirit.

  • What is Westbrook known for?

    Westbrook is known for its riverfront setting, locally rooted arts scene, and preserved natural areas like the Presumpscot River Preserve. The city hosts community festivals and has a history tied to the mills that once lined its waterways.

  • What are the best hidden gems to explore in Westbrook?

    Mill Brook Preserve is a favorite spot for peaceful hikes and springtime alewife runs. Art murals around the city and tucked-away neighborhood coffee shops give a glimpse into Westbrook's creative energy.

  • What are the best foods to try in Westbrook?

    Locally rooted dining in Westbrook often features New England seafood dishes, wood-fired pizzas, and artisan bakery treats. Visitors frequently suggest sampling seasonal produce at farmers markets or trying craft beers from area breweries.

  • What should I bring for a trip to Westbrook?

    Bring layers and a waterproof jacket to adapt to changing weather, especially if you plan to explore outdoor trails or parks. Comfortable walking shoes are useful, and a reusable water bottle comes in handy for city outings or hikes.

  • What is the nightlife in Westbrook like?

    Nightlife in Westbrook has a relaxed pace, with locally owned bars, casual restaurants, and venues hosting live music or trivia nights. Community-friendly events and gatherings create a welcoming atmosphere into the evening.

  • What are the most popular events or festivals in Westbrook?

    Westbrook hosts community events like summer concert series and craft fairs, often centered around the riverfront and local parks. Seasonal celebrations and holiday parades are also popular, inviting residents and visitors to join in.

  • Are there family friendly vacation rentals in Westbrook?

    Westbrook has a range of family-friendly vacation rentals, including houses and apartments with amenities like kitchens, multiple bedrooms, and outdoor spaces. Some hosts may provide travel cribs or high chairs for guests with young children.