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
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Westbrook vacation rentals

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.

1. 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.
$340 nightly
The price is $371
Sep 15 - Sep 16
Total with taxes and fees
Peaceful 1BR | Reading Nook | Near Portland
A snow-covered landscape with a house and a tree.

2. Serenity between the lakes and seashore

Serenity between the lakes and seashore
Westbrook
9.8 out of 10, Exceptional, (29 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.
$279 nightly
The price is $304
Sep 7 - Sep 8
Total with taxes and fees
Serenity between the lakes and seashore
A modern living room with a blue sofa, a black leather couch, and a glass of white wine on a wooden side table.

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

Modern 3BR | W/D + Parking | Near Portland
Westbrook
$405 nightly
The price is $441
Sep 7 - Sep 8
Total with taxes and fees
Modern 3BR | W/D + Parking | Near Portland
A window with a view of a snowy landscape and bare trees.

4. Tranquility between the Lakes & Sea

Tranquility between the Lakes & Sea
Westbrook
$299 nightly
The price is $326
Sep 8 - Sep 9
Total with taxes and fees
Tranquility between the Lakes & Sea
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)
"Fantastic property. Hosts were very communicative. Amazing stay. Great location! Thank you so much!"
United States
Laurie A.
$467 nightly
The price is $509
Sep 7 - Sep 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
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.
$451 nightly
The price is $492
Sep 3 - Sep 4
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.
$532 nightly
The price is $580
Sep 3 - Sep 4
Total with taxes and fees
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
A staircase with white railings and wooden steps leading to a dining area with a table and chairs.

9. 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.
$333 nightly
The price is $363
Sep 3 - Sep 4
Total with taxes and fees
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
A sandy path leading to the sea, flanked by grass fields.

10. Charming Pine Point OOB Beach Cottage Tiny House, Steps away from the beach

Charming Pine Point OOB Beach Cottage Tiny House, Steps away from the beach
Grand Beach
9.8 out of 10, Exceptional, (56 reviews)
"Stay was good. It was clean well decorated and equipped with everything you need"
United States
Tom K.
$217 nightly
The price is $237
Sep 7 - Sep 8
Total with taxes and fees
Charming Pine Point OOB Beach Cottage Tiny House, Steps away from the beach
A living room with a sofa, armchairs, a coffee table, and a potted plant.

11. Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
9.0 out of 10, Wonderful, (30 reviews)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
$174 nightly
The price is $190
Sep 3 - Sep 4
Total with taxes and fees
Beautiful 1st Floor Apartment & Amazing Shower
A modern kitchen with a wooden countertop, a glass coffee table, and a built-in shelf with kitchenware.

12. Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
10.0 out of 10, Exceptional, (33 reviews)
"Cute property.. also really suitable for long stay as the amenities were complete and near groceries and some restaurants and cafes.. convenient!"
United States
Giana
$297 nightly
The price is $324
Sep 10 - Sep 11
Total with taxes and fees
Sunny Spot with Private Parking.
A modern living room with a sofa, a coffee table, a TV, and a window with blinds.

13. Pine Point Beach private, quaint, charming studio.

Pine Point Beach private, quaint, charming studio.
Blue Point
10.0 out of 10, Exceptional, (40 reviews)
"Absolutely wonderful little place to stay in Scarborough! "
United States
Eric S.
$309 nightly
The price is $337
Sep 20 - Sep 21
Total with taxes and fees
Pine Point Beach private, quaint, charming studio.
A modern living room with a wooden dining table, a sofa, and a coffee table.

14. Furnished 1BR/1BA Walk to Maine Med/Mercy. Parking & All utilities included!

Furnished 1BR/1BA Walk to Maine Med/Mercy. Parking & All utilities included!
West End
9.2 out of 10, Wonderful, (10 reviews)
"Great place to stay - lovely building and really nicely kept, and it’s a perfect location if you want to walk down to Old Port, about 20 minutes. Would love to come back!"
United States
Cate
$419 nightly
The price is $457
Sep 9 - Sep 10
Total with taxes and fees
Furnished 1BR/1BA Walk to Maine Med/Mercy. Parking & All utilities included!
A living room with a television, a wooden chest, a glass coffee table, a sofa, and a chair.

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

Walk to Old Port ♦ West End Condo ♦ Parking
West End
9.6 out of 10, Exceptional, (90 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.
$374 nightly
The price is $408
Sep 7 - Sep 8
Total with taxes and fees
Walk to Old Port ♦ West End Condo ♦ Parking
A building with a sign for "The Send Brewing Co." and a logo featuring a stylized tree.

16. Peaceful & minutes from the Old Port with private parking

Peaceful & minutes from the Old Port with private parking
Knightville
9.8 out of 10, Exceptional, (12 reviews)
"Cute, convenient spot!"
United States
Kelly S.
$366 nightly
The price is $399
Sep 7 - Sep 8
Total with taxes and fees
Peaceful & minutes from the Old Port with private parking
A harbor with boats docked, a pier, and buildings in the background.

17. Casco Bay Vista

Casco Bay Vista
East Deering
10.0 out of 10, Exceptional, (6 reviews)
"We had a great stay at Mat's place! Convenient location, very cute apartment with a lovely view of the water. Well equipped for a couple's weekend away. We appreciated the sharp knives for cooking and the comfy couch!"
United States
Charlotte B.
$374 nightly
The price is $407
Sep 14 - Sep 15
Total with taxes and fees
Casco Bay Vista
A modern kitchen with a dining area, featuring a round table, chairs, and a hanging light fixture.

18. Elegant condo - walk to Portland's best restaurants & Old Port

Elegant condo - walk to Portland's best restaurants & Old Port
East Bayside
9.4 out of 10, Exceptional, (83 reviews)
"It was nice if you like being right in town. There is no view and it's a bit noisy."
United States
Nancy S.
Elegant condo - walk to Portland's best restaurants & Old Port
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, (39 reviews)
"Overall a pleasing stay."
United States
Mallory D.
$430 nightly
The price is $468
Sep 8 - Sep 9
Total with taxes and fees
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
A kitchen with a wooden countertop, a black kettle, a vase with flowers, and a small wire basket.

20. 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, (27 reviews)
"Great place! We would definitely return if we were in the area."
United States
Preston
$279 nightly
The price is $304
Sep 17 - Sep 18
Total with taxes and fees
Charming Studio apartment with WiFi, AC in welcoming Portland
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

10/10 Excellent
"Staff was very friendly and courteous."
Brenda 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 $166 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.

Explore a world of travel with Expedia

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.