Holiday rentals in Westbrook
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Quick stats about holiday rentals in Westbrook
Total holiday rentals
Explore 90 holiday rentals in Westbrook
Nightly prices starting at
Westbrook holiday rentals start at $39 SGD per night before taxes and fees
Verified guest reviews
Over 6,550 verified reviews to help you choose
Family-friendly holiday rentals
40 properties offer extra space & child-friendly amenities
Pet-friendly holiday rentals
Find 20 rentals that welcome pets
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Wifi availability
90 of Westbrook holiday 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!
Top-rated holiday rentals in Westbrook
Guests agree: these stays are highly rated for location, cleanliness and more.
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.
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
2BR Townhouse on Westbrook
Forget your worries in this spacious & serene space. This ultra quiet neighborhood offers a peaceful retreat from bustling city life. The tree-lined streets create a perfect setting for leisurely strolls or morning jogs. The absence of heavy traffic & urban noise makes this property a haven for those seeking a calmer environment. The property is mint & serves as the perfect home away from home. Close to downtown Westbrook, 5-mins to 95, 6-mins to airport & 15-mins to downtown Portland.
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.
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.
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.
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.
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.)
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.
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
Stylish Westbrook Studio, 10 Min to Portland
Escape to our stylish, newly renovated studio in Westbrook, just minutes from downtown Portland! Perfect for couples or solo travelers, this private apartment offers a modern, hotel-like experience with a full kitchen and free parking. Enjoy a comfortable and clean retreat with easy access to all that Maine has to offer. Comfortably fits 2 guests.
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.
Popular amenities for Westbrook holiday rentals
Other great holiday rentals in Westbrook
The "Bay of Naples Cupola Inn"
20 Min 2 Portland | Deck, Grill & Firepit | Dogs OK
The Maine Adventure
Suburban Studio Apt in a quiet family neighborhood
WINDABROOK Lodge- Recharge Reset Relax on 13 acres
Guesthouse Retreat just minutes from the Beaches!
Poet's Nook: Cozy and Private 1BR Apartment
Tranquility between the Sea & Lakes
When is the best time to visit Westbrook?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $168 SGD | $172 SGD | $168 SGD | $169 SGD | $184 SGD | $197 SGD | $220 SGD | $220 SGD | $188 SGD | $206 SGD | $190 SGD | $199 SGD |
| 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 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.
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