A frozen river with a bridge crossing over it, surrounded by buildings and parked cars.

Westbrook Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Westbrook vacation rentals

A snow-covered landscape with a house and a tree.

1. Serenity between the lakes and seashore

Serenity between the lakes and seashore
Westbrook
9.8 out of 10, Exceptional, (31 reviews)
"This is my second stay at this property and we have a third stay booked in the fall. Everything was perfect from ease of checking in and communication with the host to fully stocked kitchen and cleanliness. Highly recommend "
United States
Joanne N.
Serenity between the lakes and seashore
A modern living room with a teal sofa, two glasses of white wine, a tray of food, and a decorative candle on a wooden table.

2. Peaceful 1BR | Reading Nook | Near Portland

Peaceful 1BR | Reading Nook | Near Portland
Westbrook
10.0 out of 10, Exceptional, (1 review)
"Nicely set up and had everything needed for a comfortable stay. The entrance stairs were dingy but inside was newly decorated and well appointed. Appreciated the coffee supplies."
United States
Martha and William P.
$305 nightly
The price is $332
Oct 6 - Oct 7
Total with taxes and fees
Peaceful 1BR | Reading Nook | Near Portland
A window with a view of a snowy landscape and bare trees.

3. Tranquility between the Lakes & Sea

Tranquility between the Lakes & Sea
Westbrook
$298 nightly
The price is $325
Oct 5 - Oct 6
Total with taxes and fees
Tranquility between the Lakes & Sea
A modern living room with a blue sofa, a black leather couch, and a glass of white wine on a wooden side table.

4. Modern 3BR | W/D + Parking | Near Portland

Modern 3BR | W/D + Parking | Near Portland
Westbrook
10.0 out of 10, Exceptional, (1 review)
"Really nice and quiet place! It was suitable for our needs while we were here! Very nice host that was always making sure we had all we needed!"
United States
Ann P.
$402 nightly
The price is $438
Oct 5 - Oct 6
Total with taxes and fees
Modern 3BR | W/D + Parking | Near Portland
A dining table with two black cups and saucers, a wooden vase with flowers, and a window with white frames.

5. Modern Apartment - 20 Mins to Portland, Deck, Grill & Firepit, King Bed, DogsOK

Modern Apartment - 20 Mins to Portland, Deck, Grill & Firepit, King Bed, DogsOK
Westbrook
10.0 out of 10, Exceptional, (14 reviews)
"Excellent location, the hosts are very responsive and an absolute pleasure to work with. The home was clean, inviting and easy to check in."
United States
Bianca L.
$461 nightly
The price is $503
Oct 7 - Oct 8
Total with taxes and fees
Modern Apartment - 20 Mins to Portland, Deck, Grill & Firepit, King Bed, DogsOK
A modern living room with a teal sofa, two glasses of white wine, a tray of food, and a decorative candle on a wooden table.

6. Sleeps 16+ | W/D | Parking | 15 mins to Old Port

Sleeps 16+ | W/D | Parking | 15 mins to Old Port
Westbrook
10.0 out of 10, Exceptional, (1 review)
"This place was excellent, very clean, and the check-in/checkout process was very easy. The unit is broken into 3 distinct apartments with the upstairs being a one bedroom suite. However, all of the units are accessible to each other through stairs so it's convenient for staying connected while also having some separate space."
United States
damean s.
$867 nightly
The price is $945
Oct 6 - Oct 7
Total with taxes and fees
Sleeps 16+ | W/D | Parking | 15 mins to Old Port
A bedroom with a large bed, white curtains, and a view through the windows.

7. Cozy 3BR | Pet Friendly | Near Portland | Parking

Cozy 3BR | Pet Friendly | Near Portland | Parking
Westbrook
10.0 out of 10, Exceptional, (14 reviews)
"We had a great stay here. It was very clean and conveniently located."
United States
Angela B.
$402 nightly
The price is $438
Oct 5 - Oct 6
Total with taxes and fees
Cozy 3BR | Pet Friendly | Near Portland | Parking
A dirt path in a park with autumn foliage.

8. WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres

WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
Westbrook
9.6 out of 10, Exceptional, (43 reviews)
"Host was excellent, even thinking of bug spray, yoga mats, binoculars, and extra blankets. We loved our stay!"
United States
Genevieve W.
$577 nightly
The price is $629
Oct 5 - Oct 6
Total with taxes and fees
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
A bedroom with a bed, a nightstand, a lamp, a door, and a staircase.

9. Great suburban location close to town!

Great suburban location close to town!
Deering Center
10.0 out of 10, Exceptional, (1 review)
"Small but cozy space, well kept, good value for the price and has all the amenities you could expect. Would be happy to stay here again."
United States
Peter H.
$95 nightly
The price is $97
Oct 25 - Oct 26
Total with taxes and fees
Great suburban location close to town!
A living room with a sofa, armchair, and glass coffee table. There are two lamps on side tables and a window with curtains.

10. Portland 1-bedroom with enclosed porch & parking

Portland 1-bedroom with enclosed porch & parking
Deering Center
8.2 out of 10, Very good, (15 reviews)
"As expected."
United States
Lance
$109 nightly
The price is $111
Oct 13 - Oct 14
Total with taxes and fees
Portland 1-bedroom with enclosed porch & parking
A gym with treadmills, elliptical machines, and exercise balls.

11. 1-bedroom hotel suites in Scarborough with essentially stocked kitchens.

1-bedroom hotel suites in Scarborough with essentially stocked kitchens.
South Portland
9.2 out of 10, Wonderful, (20 reviews)
"We really appreciated our stay!"
United States
Anonymous traveler
$164 nightly
The price is $178
Oct 6 - Oct 7
Total with taxes and fees
1-bedroom hotel suites in Scarborough with essentially stocked kitchens.
A bedroom with a wooden bed, a nightstand, a bench, a chair, and a ceiling with a light fixture.

12. Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.4 out of 10, Very good, (21 reviews)
"I will admit the location and surrounding areas are a bit sketchy, but, once inside, we felt super secure. There are multiple doors and gates with locks to ensure safety. Place was clean and had everything we needed for a quick stay."
United States
Krysta
$149 nightly
The price is $151
Nov 1 - Nov 2
Total with taxes and fees
Studio Apartment near downtown Walkable!
A living room with a sofa, armchairs, a coffee table, and a potted plant.

13. Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
9.0 out of 10, Wonderful, (32 reviews)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
$166 nightly
The price is $181
Oct 7 - Oct 8
Total with taxes and fees
Beautiful 1st Floor Apartment & Amazing Shower
A staircase with white railings and wooden steps leading to a dining area with a table and chairs.

14. 1200 sq ft ♦ West End Townhouse ♦ Perfect Location

1200 sq ft ♦ West End Townhouse ♦ Perfect Location
West End
8.4 out of 10, Very good, (61 reviews)
"Nice place, good location and very responsive host. I would definitely stay again when in Portland."
United States
Susan d.
$356 nightly
The price is $388
Oct 29 - Oct 30
Total with taxes and fees
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
A kitchen with a wooden countertop, a black kettle, a vase with flowers, and a small wire basket.

15. Charming Studio apartment with WiFi, AC in welcoming Portland

Charming Studio apartment with WiFi, AC in welcoming Portland
Munjoy Hill
9.6 out of 10, Exceptional, (29 reviews)
"Loved this spot and would stay again. Had everything you needed and a great location. Cute little attic spot but nice and cool."
United States
Emily N.
$212 nightly
The price is $231
Nov 1 - Nov 2
Total with taxes and fees
Charming Studio apartment with WiFi, AC in welcoming Portland
A kitchen with wooden cabinets, a stainless steel sink, and a potted plant.

16. Bright & Spacious Apartment with Amazing Shower

Bright & Spacious Apartment with Amazing Shower
Parkside
8.6 out of 10, Excellent, (27 reviews)
"Lovely apartment, in a pristine location. Very spacious and comfortable all around. Highly recommended this place for your next stay in Portland, Maine!"
United States
Gintare V.
$183 nightly
The price is $200
Oct 28 - Oct 29
Total with taxes and fees
Bright & Spacious Apartment with Amazing Shower
A living room with a television, a wooden chest, a glass coffee table, a sofa, and a chair.

17. Walk to Old Port ♦ West End Condo ♦ Parking

Walk to Old Port ♦ West End Condo ♦ Parking
West End
9.6 out of 10, Exceptional, (91 reviews)
"Was great for our few days in Portland! Having a designated parking space was great and the location was convenient for everything we wanted to do."
United States
Britney G.
$347 nightly
The price is $378
Oct 26 - Oct 27
Total with taxes and fees
Walk to Old Port ♦ West End Condo ♦ Parking
A street lined with buildings, one with a red door and a sign that reads "MINATO".

18. Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (149 reviews)
"Owner was so accommodating!"
United States
Kiernan
$262 nightly
The price is $286
Oct 20 - Oct 21
Total with taxes and fees
Adorable Portland getaway on the Eastern Promenade
A modern house with a wooden exterior, a small garden, and a visible window.

19. Spacious and Contemporary Condo in the Heart of Portland - Close to Beach

Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
East Bayside
8.8 out of 10, Excellent, (40 reviews)
"Overall a pleasing stay."
United States
Mallory D.
$429 nightly
The price is $467
Oct 15 - Oct 16
Total with taxes and fees
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
A two-story house with a covered front porch and a brick foundation.

20. Luxury on Back Cove - Three Gables

Luxury on Back Cove - Three Gables
Rosemont
10.0 out of 10, Exceptional, (15 reviews)
"GoodLocation, very clean. Would stay again "
United States
Carly B.
$501 nightly
The price is $547
Nov 4 - Nov 5
Total with taxes and fees
Luxury on Back Cove - Three Gables
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Westbrook Hotel Reviews

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

8/10 Good
"Ok"
Carlo 1-night trip
Posted less than an hour ago
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

Find out more about Westbrook

Everything you need to know about Westbrook vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Westbrook vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Westbrook vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Westbrook vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Westbrook. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Westbrook in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $151 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Westbrook rentals

At Expedia, we put the best Westbrook vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Westbrook rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Westbrook vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Westbrook. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Frequently asked questions

Can I find vacation rentals in Westbrook?

Yes, we have vacation rentals in Westbrook near Westbrook Performing Arts Center, or you can choose a secluded option if you want a relaxing stay. The shops and restaurants are several reasons why visitors like Westbrook. While you're here, grab a bite or have a drink at the coffeehouses.

What's the top vacation rental in Westbrook?

Quintessential Maine Beach Cottage: Visitors like this Westbrook vacation home rental. It is located on the beach and has a private yard, a selection of games, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a full-sized fridge, a dishwasher, and a stovetop, so you can cook with friends or family.

How many vacation rentals will I find in Westbrook?

With 10 Expedia vacation rentals, you're sure to find just the right place for your Westbrook stay.

What’s there to see and do in Westbrook?

Family-friendly attractions include Happy Wheels Skate Center, whereas MAGAN Trailhead is a spot to enjoy the outdoors. In the larger area, you’ll find Westbrook Performing Arts Center and Maine Mall.

What’s a vacation rental in Westbrook like?

Vacation rentals are privately owned properties you can stay in for several days or longer in Westbrook. Vacation rentals feature amenities like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from shared hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a family getaway.