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
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Westbrook vacation rentals

Dining

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.
$367 nightly
The price is $400
Aug 9 - Aug 10
Total with taxes and fees
Peaceful 1BR | Reading Nook | Near Portland
Interior

2. Tranquility between the Lakes & Sea

Tranquility between the Lakes & Sea
Westbrook
$357 nightly
The price is $389
Aug 5 - Aug 6
Total with taxes and fees
Tranquility between the Lakes & Sea
Dining

3. 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, (11 reviews)
"Fantastic property. Hosts were very communicative. Amazing stay. Great location! Thank you so much!"
United States
Laurie A.
$459 nightly
The price is $501
Aug 5 - Aug 6
Total with taxes and fees
Modern Apartment - 20 Mins to Portland, Deck, Grill & Firepit, King Bed, DogsOK
3 bedrooms, premium bedding, iron/ironing board, travel crib

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

Cozy 3BR | Pet Friendly | Near Portland | Parking
Westbrook
10.0 out of 10, Exceptional, (13 reviews)
"We had a great stay here. It was very clean and conveniently located."
United States
Angela B.
$436 nightly
The price is $475
Aug 24 - Aug 25
Total with taxes and fees
Cozy 3BR | Pet Friendly | Near Portland | Parking
Dining

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

Sleeps 16+ | W/D | Parking | 15 mins to Old Port
Westbrook
$1,032 nightly
The price is $1,125
Aug 9 - Aug 10
Total with taxes and fees
Sleeps 16+ | W/D | Parking | 15 mins to Old Port
Property grounds

6. 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.
$529 nightly
The price is $577
Aug 5 - Aug 6
Total with taxes and fees
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
1 bedroom, WiFi, bed sheets

7. Studio Apartment near downtown Walkable!

Studio Apartment near downtown Walkable!
West Bayside
8.2 out of 10, Very Good, (12 reviews)
"A perfectly decent place to stay, plenty of restaurants and bars within reasonable walking distance. Neighborhood is a bit rough, as the listing mentioned, but no problems while I was there. Response time on questions to the host could be better."
Canada
Brian
$188 nightly
The price is $189
Aug 5 - Aug 6
Total with taxes and fees
Studio Apartment near downtown Walkable!
Interior

8. Sunny Spot with Private Parking.

Sunny Spot with Private Parking.
Knightville
10.0 out of 10, Exceptional, (31 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
$298 nightly
The price is $325
Sep 1 - Sep 2
Total with taxes and fees
Sunny Spot with Private Parking.
Beach nearby, sun loungers, beach towels

9. 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, (51 reviews)
"Stay was good. It was clean well decorated and equipped with everything you need"
United States
Tom K.
$247 nightly
The price is $269
Aug 10 - Aug 11
Total with taxes and fees
Charming Pine Point OOB Beach Cottage Tiny House, Steps away from the beach
Interior

10. 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."
United States
Rob M.
$381 nightly
The price is $416
Aug 11 - Aug 12
Total with taxes and fees
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
Exterior detail

11. Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (139 reviews)
"Owner was so accommodating!"
United States
Kiernan
$363 nightly
The price is $396
Aug 10 - Aug 11
Total with taxes and fees
Adorable Portland getaway on the Eastern Promenade
Property grounds

12. 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, (38 reviews)
"Overall a pleasing stay."
United States
Mallory D.
$433 nightly
The price is $471
Aug 25 - Aug 26
Total with taxes and fees
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
Flat-screen TV, Netflix, books, streaming services

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

Walk to Old Port ♦ West End Condo ♦ Parking
West End
9.6 out of 10, Exceptional, (88 reviews)
"It was what we were looking for- in Portland, with a parking spot. Some nice restaurants nearby- walking distance! Note the bathroom is on the first floor, bedrooms are on second. Modest but had everything we needed! What we were disappointed in was we had no idea how many museums and local attractions in a city are closed till the end of April or May! "
United States
Susan R.
$391 nightly
The price is $426
Sep 2 - Sep 3
Total with taxes and fees
Walk to Old Port ♦ West End Condo ♦ Parking
Interior

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

Charming Studio apartment with WiFi, AC in welcoming Portland
Munjoy Hill
9.4 out of 10, Exceptional, (22 reviews)
"Great place! We would definitely return if we were in the area."
United States
Preston
$289 nightly
The price is $315
Aug 31 - Sep 1
Total with taxes and fees
Charming Studio apartment with WiFi, AC in welcoming Portland
Dining

15. 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, (81 reviews)
"I had a wonderful week at this perfect place. Met my expectations and way more. So walkable all over Portland. I will be back. Thank you so very much."
United States
Margaret H.
$471 nightly
The price is $513
Aug 23 - Aug 24
Total with taxes and fees
Elegant condo - walk to Portland's best restaurants & Old Port
Exterior detail

16. 1200 Sq Ft ♦ West End Gem ♦ Perfect Location

1200 Sq Ft ♦ West End Gem ♦ Perfect Location
West End
9.2 out of 10, Wonderful, (105 reviews)
"Very nice place, clean, good location. On-street parking was available. Second floor kitchen & bath, so not for those with issues with stairs, but fine for us. Would stay again!"
United States
Gary
$270 nightly
The price is $295
Aug 31 - Sep 1
Total with taxes and fees
1200 Sq Ft ♦ West End Gem ♦ Perfect Location
Smart TV

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

Pine Point Beach private, quaint, charming studio.
Blue Point
10.0 out of 10, Exceptional, (38 reviews)
"Absolutely wonderful little place to stay in Scarborough! "
United States
Eric S.
$320 nightly
The price is $349
Sep 1 - Sep 2
Total with taxes and fees
Pine Point Beach private, quaint, charming studio.
Smart TV

18. Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
9.2 out of 10, Wonderful, (29 reviews)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
$310 nightly
The price is $338
Aug 9 - Aug 10
Total with taxes and fees
Beautiful 1st Floor Apartment & Amazing Shower
Outdoor dining

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

Peaceful & minutes from the Old Port with private parking
Knightville
9.6 out of 10, Exceptional, (10 reviews)
"Jennifer’s VRBO is exactly as cute, clean and cozy as the listing’s photos depict. It is so well maintained that she has living house plants that are thriving 10/10. I can’t wait to stay again!"
United States
Liz P.
$366 nightly
The price is $399
Sep 4 - Sep 5
Total with taxes and fees
Peaceful & minutes from the Old Port with private parking
Dining

20. 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
9.4 out of 10, Exceptional, (6 reviews)
"All was great...clean and convenient."
United States
Krista P.
$450 nightly
The price is $491
Aug 17 - Aug 18
Total with taxes and fees
Furnished 1BR/1BA Walk to Maine Med/Mercy. Parking & All utilities included!
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

Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

10/10 Excellent
"The staff at the hotel was extremely friendly & welcoming. Richard at the front desk made us feel like part of the family. Alex was also extremely helpful. I highly recommend this place as it’s very conveniently located to many wonderful places like downtown, the art museum, old port etc."
Nirupma 2-night trip
Posted less than an hour ago
Holiday Inn Portland-By the Bay by IHG

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 $189 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?

New Listing. 2BR+Bonus Sleeping Room in OOB. Walk to Beach & Amusement Park.: Visitors like this Westbrook vacation home rental. It is located near the beach and offers a patio, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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.