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Westbrook vacation rentals

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Top-rated vacation rentals in Westbrook

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

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Rental unit in Westbrook

4.93 out of 5 average rating, 123 reviews

Riverside Retreat: Cozy Charm Near Portland!

This bright and sunny 3rd floor unit resides in a recently renovated historic 1890 home on a corner lot of the desirable Pleasant Street neighborhood. Experience the up and coming Westbrook community while close to everything Portland has to offer! Amenities Include off street parking, an updated kitchen with white granite countertops, updated bathroom, brand new bed with premium linens, stained glass window, skylight, beautiful hardwood floors throughout, and Smart TV with Netflix and Sling.

Rental unit in Westbrook

4.89 out of 5 average rating, 122 reviews

Private Apt in Spacious Victorian-Style House

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 and a cozy twin bed in the living room. We also have an air mattress and a Pack 'n Play available.

Guest suite in Portland

4.97 out of 5 average rating, 189 reviews

Sunflower Retreat in North Back Cove

The Sunflower Retreat is a private, self-contained, peaceful hideaway. Located in the back half of an adorable 1920's home, this BnB space has everything you could need. A driveway leads you around to the back of the house, where a stone walkway guides you to your own private patio and entrance. A comfortable queen bed, kitchenette, full bathroom, closet, dining nook, black-out curtains, eatery, and television are included. Free street parking. Located in close proximity of many things!

Rental unit in Windham

4.99 out of 5 average rating, 136 reviews

The Roost - lovely one bedroom efficiency unit

Staying at the Roost means you will be 15 minutes to the ocean, the airport and to the Old Port; 10 minutes to nearby lakes and rivers; 5 minutes to everything downtown Westbrook has to offer, including many restaurants, parks, live music venues, shopping and a movie theater: what you are looking for is nearby! Kick back and relax in this calm, stylish space with a queen-sized bed, kitchenette, dining/work area, excellent wifi, a full bathroom and a big yard.

Cottage in Portland

4.89 out of 5 average rating, 529 reviews

Cozy & Quiet Modern Cottage

Modern studio cottage designed and maintained with sustainability and eco-friendliness in mind, located in a quiet Portland neighborhood only a 7-10 minute drive (and $10 Uber/Lyft ride) from downtown Portland, the Old Port, and all local visitor attractions. The cottage is a mile down the road from the Allagash Brewing complex and is within walking distance (.5 mi) of the restaurants and bars at Morrill's Corner. This is an LBGTQIA- and BIPOC-friendly space.

Guesthouse in Windham

4.99 out of 5 average rating, 250 reviews

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.

Home in Westbrook

4.89 out of 5 average rating, 506 reviews

Reno Barn w/ a lot of Charm! Breweries & Airport

** Cozy Renovated Barn w/ artist loft ** Minutes from airport and within walking distance to the Allagash Brewing Company & other breweries. Lots of hiking trails along the Presumpscot River. Short drive to downtown Portland, restaurants, music venues, beaches, lighthouses and nightlife. Barn is located in a quiet area ~ relax on the back deck with a glass of wine star gazing. Come check us out!!

Guesthouse in Cumberland

4.96 out of 5 average rating, 200 reviews

Cottage Under a Crabapple Tree

Steps from extensive nature trails and wildflower meadows, this quaint studio cottage is nestled conveniently between the restaurants and breweries of Portland, the outlet shopping of Freeport, and miles and miles of rocky coastline. Perfect for a quiet Maine getaway, lodging near Cumberland fairgrounds and other local attractions, or a visit to family and friends in the area.

Farm stay in Gray

4.94 out of 5 average rating, 270 reviews

Great Goat Get-away in Southern Maine!

This quiet and cozy house is located in the woods at the renowned Ten Apple Farm. Centrally located in Southern ME, we're just a short drive from Portland, lakes, ski areas, LL Bean and more! On the farm you can meet and interact with our herd of goats, sheep, pigs and chickens, learn to milk, collect eggs, and arrange on of our famous goat hikes!

Rental unit in Portland

4.96 out of 5 average rating, 186 reviews

Compact & Complete in residential neighborhood

Completely renovated ground level apartment in Deering section of Portland. Walk to off-peninsula restaurants, coffee and wine shops. Nearby trails for walking or biking. Near UNE's Portland Campus. On bus line to easily reach downtown Old Port area, USM and other attractions. Off street parking for your car. Portland STHR-0010302019

Rental unit in Westbrook

4.88 out of 5 average rating, 194 reviews

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.

Home in Lisbon

4.93 out of 5 average rating, 389 reviews

Unplug at a Beachy Bolthole with Classic New England Style

Chill on the porch after exploring a scenic local walking trail and soak up the serenity of this breezy blue and white hideaway. Striped oars, starfish, smooth shells, and ocean scenes blend with shades of teal and aqua for a thoroughly calm space. There are EV chargers behind the post office. It’s around a block and a half.

Vacation rentals for every style

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Popular amenities for Westbrook vacation rentals

Laptop-friendly workspace

Air conditioning

Stay near Westbrook's top sights

Allagash Brewing Company155 locals recommend

The Maine Mall86 locals recommend

Maine Mall86 locals recommend

Portland International Jetport50 locals recommend

Bull Jagger Brewing Company38 locals recommend

Mast Landing Brewing Company30 locals recommend

Other great vacation rentals in Westbrook

Tiny home in Gorham

5 out of 5 average rating, 22 reviews

The Chickadee Tiny House

Guesthouse in Cape Elizabeth

4.98 out of 5 average rating, 173 reviews

Newly built private guest suite off Shore Road

Guest suite in East End

4.97 out of 5 average rating, 633 reviews

PRlVATE SUlTE in the Heart of East End Portland

Rental unit in Westbrook

4.94 out of 5 average rating, 17 reviews

Suburban Studio Apt in a quiet family neighborhood

Home in Westbrook

4.9 out of 5 average rating, 69 reviews

Quaint farmhouse master suite w/private bath

Condo in Scarborough

4.96 out of 5 average rating, 334 reviews

Cozy condo by the beach!

Barn in Freeport

5 out of 5 average rating, 157 reviews

Cozy Maine Barn Hideaway- 2nd Floor Apartment

Guest suite in Gorham

4.97 out of 5 average rating, 79 reviews

Countryside Getaway Private Guest Apartment

Quick stats about vacation rentals in Westbrook

Total rentals
100 properties
Nightly prices starting at
$40 before taxes and fees
Total number of reviews
5.8K reviews
Family-friendly rentals
50 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
50 properties have a dedicated workspace

Frequently Asked Questions

Where should I stay in Westbrook?
Make yourself at home in Westbrook by choosing from our most frequently booked neighborhoods. We have over 520 vacation rentals in Stroudwater, over 400 vacation rentals in Nasons Corner, and over 390 vacation rentals in Riverton.
Are there pet-friendly vacation rentals in Westbrook?
Four-legged friends are welcome in Westbrook. Choose from more than 30 vacation rentals for guests traveling with pets.
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 $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly apartment rentals in Westbrook?
Westbrook has more than 10 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do apartment rentals in Westbrook have air conditioning?
Absolutely! We offer over 20 apartment rentals with air conditioning in Westbrook. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Westbrook have wireless internet?
Absolutely! We offer over 40 house rentals with wireless internet in Westbrook. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Westbrook?
Enhance your stay in our House Rentals with the most popular amenities: over 40 homes with air conditioning, over 40 homes with wireless internet, and more. Indulge in the ultimate retreat, tailored to your preferences.

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