House vacation rentals in Westbrook

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Top-rated house rentals in Westbrook

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Top guest favorite
A spacious living area features two light-colored sofas arranged around a round white coffee table. A geometric rug with blue accents sits beneath the seating. Natural light floods the room through a corner window, with simple decor enhancing the serene ambiance.
Home in Deering Center
4.96 out of 5 average rating, 359 reviews

Explore Portland from a 18th-Century Victorian

*Covid-Clean* Cook breakfast in a bright kitchen with robust hardwood floors in this calm Victorian home. Sit down at a traditional dining table in an open-plan room featuring vivid wood-paneled walls, serene decor, and a geometric rug with pops of blue. Bright and spacious with entire top floor privacy. ** NO SHARED SPACE** This is a dedicated Airbnb apartment with no shared space whatsoever. Ultimate privacy. This apartment can be rented as (1) bedroom for up to (2) guests or as (2) bedroom for up to (4) guests. It is $50/night additional cost for the (2) bedroom. Please confirm the second bedroom is available if interested. Either option has a full bathroom with claw foot tub and shower. Full service kitchen with stove, refrigerator and microwave for your private use. Large living room with (2) couches and flat screen. The very large master bedroom with the ultra comfortable king size mattress also has cable tv. . Both the one bedroom and two bedroom option have their own private entrance, private kitchen and bath on the third floor. No shared space with anyone else with either the one or two bedroom rental options. Private entrance. Spacious one or two bedroom apartment with full kitchen, bath and living room as well as other amenities. We are available for any questions or concerns but as a rule we give the guests their privacy. The house is steps away from some of Portland’s most popular eateries including the Knotted Apron, Woodfords Bar and Grill, Bird and Co., The Treehouse, and Elsmere BBQ. Not far to the Old Port area to browse seafood markets and shops. Visit the Portland Observatory to explore a historic lighthouse. Close to all public transportation and Portland International Airport Parking in the driveway is a possibility, please ask if interested. Street parking is available, it is based on an odd /even system of the street address. You want to be parked on the same side as the date would be at 12:01 AM on any given day. You are staying at 32 Lawn Ave

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
4.89 out of 5 average rating, 293 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 favorite
Home in Westbrook
4.89 out of 5 average rating, 595 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.

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 North Deering
4.96 out of 5 average rating, 153 reviews

"Good Vibes" 4 Wonderful Seasons @ Portland Home!

Your crew 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, no loud partying after 10 pm. City of Portland License #: STHR-004465-2022

Top guest favorite
A charming waterfront cottage is presented with a bright blue door and two red chairs on a stone patio. Lush greenery surrounds the property, enhancing its inviting exterior. The tranquil waters of Pettingill Pond can be seen in the background, reflecting the sky.
Home in Windham
4.95 out of 5 average rating, 179 reviews

Waterfront Gem walkable to Restaurants!

Waterfront Oasis on Pettingill Pond. You couldn't get any closer to the water, it's steps away. There are 3 Kayaks, and a paddleboat, firepit and dock for guest use! This a great spot for swimming and watersports! This home has been newly renovated, the effect results in a simple, stylish, comfortable space for guests to enjoy. Walk to Franco's Bistro for from Scratch Italian food, or Bob's Seafood for a fish taco! This is a piece of paradise on sweet Pettingill Pond in the heart of Windham.

Top guest favorite
The house is nestled among trees by Highland Lake, featuring a rustic exterior with shingles. A large deck is visible, equipped with multiple outdoor seating options. Stairs lead from the water to the deck, providing direct access to the home.
Home in Falmouth
4.96 out of 5 average rating, 102 reviews

Beautiful lake-side home close to Portland Maine

A peaceful & charming renovated old home with private dock on Highland Lake, Falmouth Maine, 20 mins from Portland. *Contact us for longer winter availability! **June/July/Aug, Sat-Sat 7 day min Enjoy beautiful sunsets, canoeing, kayaking, paddle-boarding or fishing on the lake. Or take a short drive to downtown Portland, visit Old Port restaurants & bars, local breweries, Freeport outlet shopping, ski resorts, hiking and walking trails, golf courses, indoor/outdoor cinemas, and more!

Top guest favorite
A two-story Victorian house is framed by large trees and a white picket fence. Lush greenery surrounds the home, enhancing the exterior’s classic charm. Multiple windows reflect natural light, while a staircase leads to the front door, inviting guests into the space.
Home in Portland
4.99 out of 5 average rating, 156 reviews

Distinctive Home & Garden

Beautiful renovated Victorian with artistic interior, hardwood floors, gourmet kitchen, patio, mature garden. Within minutes of downtown, restaurants, shopping & Back Cove. Comfortable & fully equipped. Our home was featured in Old Port magazine. Please search the article by inserting "oldport/people/urban-oasis" We have been inspected by the City of Portland and are in compliance with all safety and alarm requirements. Officially licensed to operate as an Airbnb site. # 20185315-ST

Top guest favorite
An open living area is highlighted by large windows that frame scenic views of the marsh. A modern gas fireplace serves as a focal point, while a light-colored sofa and a small table with a plant create a welcoming ambiance. Bar seating for four extends to the kitchen.
Home in Higgins Beach
5 out of 5 average rating, 104 reviews

Higgins Beach *New* Beach Home & Private Offices

Custom designed contemporary at the beach. Perfect for a relaxing getaway, visiting family and friends or working remotely. Chef's kitchen w/ high end appliances, granite countertops, enclosed porch grill area. 3 bedrooms and 2 private offices Huge windows and amazing views from all of the rooms highlight the natural beauty of high tides, sun rises and sun sets. Wonderful beachfront walks and beautiful surroundings inside and out. Easy proximity to Portland's Old Port.

Top guest favorite
A spacious backyard features a landscaped area with vibrant flowers and stone terraces. The home, set above, includes an elevated deck shaded by a canopy. Lush greenery surrounds the property, providing a sense of seclusion in a serene environment.
Home in Gorham
4.99 out of 5 average rating, 166 reviews

Beautiful Home In Gorham Maine

Well appointed, bright and sunny apartment for two people in a quiet neighborhood. Large private back yard, formal gardens and pond, elevated deck, well stocked kitchen. 25 mins. to downtown Portland and the seacoast area. Minutes to local nature trails, swimming, kayaking, dining, supermarket & bakeries. ** NO PROFILE/REVIEWS? please provide a little info about whose coming, ie, name/age/occupation, reason of visit, etc, and any other info you wish to provide. Thank you!

Top guest favorite
The exterior of a red barn-style home is surrounded by lush greenery and colorful flower beds. A patio setup includes comfortable seating, a dining table with an umbrella, and a fire pit on a pebbled area, providing an inviting outdoor space.
Home in New Gloucester
4.97 out of 5 average rating, 149 reviews

The Barnhouse with hot tub

Get away with your whole family at this peaceful home in the country. Hear the frogs chirping in the pond, birds tweeting in the treetops and watch chickens roam around. Enjoy the clear, starry nights while relaxing in the hot tub or cozying up by the fire. Centrally located between coast and mountains. Head a hour north to take the family hiking or on the slopes to enjoy the mountains. Head 40 minutes south to take in the coast and see the iconic Maine lighthouse.

Top guest favorite
The Birch Ledge Guest House is a two-story structure nestled among trees, featuring a rustic exterior with a metal roof. A small patio with two chairs is positioned at the entrance, and a staircase leads to the loft area. Lush greenery surrounds the home.
Home in Hollis
4.99 out of 5 average rating, 467 reviews

Birch Ledge Guesthouse--Four Season Maine Getaway

Both rustic and elegant, the Birch Ledge Guest House offers a cozy place to relax and recharge, whatever the season. The first floor features a spacious living room (with queen sized pull-out-couch), dining area, and small kitchen. The bathroom has a walk-in shower. The second floor is a loft accessible by a spiral staircase and has a comfy queen and two twin sized beds. The guesthouse is surrounded by quiet forest and is an easy 30 minute drive to Portland.

Top guest favorite
A living area features a light-colored sofa paired with a leather armchair. A large mirror hangs on the wall, reflecting the space. Decorative art pieces are framed and displayed. A blue side table complements the warm wood flooring.
Home in West End
4.97 out of 5 average rating, 150 reviews

2 bed house w/king bed, pets & off-street parking!

Welcome to the 1840s Farm Hand’s House 800sqft West End house • off-street parking directly behind house (plz confirm car size) • King bed in primary bedroom • 90 walk score • dog friendly! (fee applies) • fast wifi • 3 min drive to S. Portland • 10 min drive to beaches • 5 min walk to renowned restaurants & coffee • 10 min walk to Old Port • Free W/D in first floor • Residential street • 1840s house with some quirks Max 3 adults unless you message ahead

Popular amenities for Westbrook house rentals

When is the best time to visit Westbrook?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$37,192 GYDG$37,610 GYDG$35,102 GYDG$34,893 GYDG$37,819 GYDG$46,803 GYDG$64,772 GYDG$46,803 GYDG$47,848 GYDG$35,311 GYDG$34,058 GYDG$37,610 GYD
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Quick stats about house rentals in Westbrook

  • Total vacation rentals

    Explore 40 vacation rentals in Westbrook

  • Nightly prices starting at

    Westbrook vacation rentals start at G$8,358 GYD per night before taxes and fees

  • Verified guest reviews

    Over 2,310 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Westbrook vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Westbrook rentals

  • 4.7 Average rating

    Westbrook stays receive an average rating of 4.7 out of 5 from guests

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