
Vacation rentals in Westbrook
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Top-rated vacation rentals in Westbrook
Guests agree: these stays are highly rated for location, cleanliness, and more.

* Cozy Cottage * 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.

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

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!

Maine Escape | 9mi Portland • 6mi to Beach
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!

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.

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.

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.

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 in the cabin. Please, no smokers, kids under 7, or guest pets. STHR-000718-2018

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 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.

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.

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!
Popular amenities for Westbrook vacation rentals
Other great vacation rentals in Westbrook

Cozy, Artsy Lair in Westbrook

Charming Portland Getaway

Yurtvana

Private 2 Bedroom Ranch in Frenchtown

20 Min 2 Portland | Deck, Grill & Firepit | Dogs OK

Updated Studio Apartment

Historic Maine Barn with Private Saltwater Hot Tub

Cozy Lakefront Cabin-Private Dock-Kayaks-Firepit
When is the best time to visit Westbrook?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R2,084 ZAR | R1,968 ZAR | R1,934 ZAR | R2,184 ZAR | R2,368 ZAR | R2,535 ZAR | R2,835 ZAR | R2,835 ZAR | R2,418 ZAR | R2,651 ZAR | R2,451 ZAR | R2,568 ZAR |
| Avg. temp | -4°C | -3°C | 1°C | 7°C | 13°C | 18°C | 21°C | 21°C | 16°C | 10°C | 4°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 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.
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 house rentals in Westbrook?
Experience the best of Westbrook with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Quick stats about vacation rentals in Westbrook

Total vacation rentals
Explore 90 vacation rentals in Westbrook

Nightly prices starting at
Westbrook vacation rentals start at R500 ZAR per night before taxes and fees

Verified guest reviews
Over 6,550 verified reviews to help you choose

Family-friendly vacation rentals
40 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
90 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!
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