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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.

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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, 687 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.

Top guest favorite
Home in Westbrook
4.89 out of 5 average rating, 617 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.

Top guest favorite
Apartment in Westbrook
5 out of 5 average rating, 21 reviews

Private studio nestled in woods

New roomy studio located in a quiet residential neighborhood minutes from Portland. Guests access the apartment via their private deck and entrance. Full kitchen (stocked with cooking essentials and dishwasher), washer/dryer, and private parking for your convenience. Our goal is to be inclusive and welcoming to all. *Note: You must go up a full staircase to access apartment. The space is open to the stairs and therefore not safe for some children. Off-season discounted monthly rate available.

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
4.89 out of 5 average rating, 360 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
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, 32 reviews

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

Welcome to River's Edge Retreat! Our spacious, dog-friendly apartment is ideal for exploring Portland and beyond. With room for 8 and all the comforts of home, it's your cozy base for adventure. Sip coffee on the private deck, unwind by the firepit, or stroll to Westbrook’s shops and cafes. After a day of sightseeing, relax in comfort just 20 minutes from Portland’s vibrant Old Port. 15 Minute Walk to Downtown Westbrook 20 Minute Drive to Downtown Portland 12 Minute Drive to USM Gorham

Top guest favorite
A cozy sleeping area features a queen size bed dressed in light-colored bedding with a patterned throw. Nightstands with lamps provide soft illumination, while a decorative wall hanging and a small window allow natural light to enter the space.
Apartment in Westbrook
4.97 out of 5 average rating, 36 reviews

Suburban Studio Apt in a quiet family neighborhood

Kick back and relax in this calm, stylish space. Studio apartment is a spacious hotel room with homey amenities like a washer and dryer, kitchenette, free WiFi and off street parking. This apartment is located in Westbrook, just outside of Portland. Very convenient to I-95 and the Portland Jetport. This is in a quiet, family friendly neighborhood. It is a short drive from downtown Westbrook. It is a 20-25 minute drive to the Old Port section of Portland, depending on traffic.

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, 118 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.

Guest favorite
The exterior of a charming Victorian building is displayed, featuring a distinctive turret and a combination of blue walls with white trim. A spacious porch and steps lead up to the entrance. Surrounding trees provide a touch of greenery, while parked vehicles are visible in the nearby area.
Apartment in Westbrook
4.91 out of 5 average rating, 135 reviews

Minutes to Portland | Spacious | One Bedroom

Conveniently located in the charming Cumberland Mills neighborhood of Westbrook, this spacious one bedroom Victorian apartment offers easy access to Portland, the jetport, the highway, Rock Row, and other Westbrook attractions. Delicious eateries, local breweries, and Riverbank Park are within walking distance. This apartment comes fully furnished with a comfortable queen bed in the bedroom, a dedicated workspace, and a Pack n' Play (please bring your own linens).

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 Westbrook
4.98 out of 5 average rating, 58 reviews

Riverfront guest house w/ patio

A beautiful one-bedroom guest suite with kitchenette and private entrance overlooking the river makes a perfect launching point for all that Portland and southern Maine have to offer. A comfortable oasis for one or two people. Bright, recently renovated with gleaming maple floors and large windows. Downtown Westbrook is a short walk away, with live music, great restaurants, an award-winning brewery, a bakery and coffee shop, great shops, and even a cat lounge.

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, 141 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.

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 Portland
5 out of 5 average rating, 471 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 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 beverage in one of our comfy Adirondacks.

Top guest favorite
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
4.95 out of 5 average rating, 531 reviews

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

Popular amenities for Westbrook vacation rentals

When is the best time to visit Westbrook?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$27,207 GYDG$27,835 GYDG$27,207 GYDG$27,416 GYDG$29,718 GYDG$31,811 GYDG$35,578 GYDG$35,578 GYDG$30,346 GYDG$33,276 GYDG$30,765 GYDG$32,230 GYD
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.

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 G$6,279 GYD 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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