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.
The price is ￥24,385
￥62,933 total
includes taxes & fees
Aug 9 - Aug 10
Peaceful 1BR | Reading Nook | Near Portland
Interior

2. Tranquility between the Lakes & Sea

Tranquility between the Lakes & Sea
Westbrook
The price is ￥36,026
￥73,907 total
includes taxes & fees
Aug 11 - Aug 12
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.
The price is ￥41,131
￥88,560 total
includes taxes & fees
Aug 12 - Aug 13
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.
The price is ￥31,936
￥78,880 total
includes taxes & fees
Aug 24 - Aug 25
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
The price is ￥80,705
￥176,966 total
includes taxes & fees
Aug 9 - Aug 10
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.
The price is ￥63,573
￥91,415 total
includes taxes & fees
Aug 11 - Aug 12
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
The price is ￥18,219
￥30,061 total
includes taxes & fees
Aug 11 - Aug 12
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
The price is ￥31,075
￥51,237 total
includes taxes & fees
Sep 1 - Sep 2
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, (52 reviews)
"Stay was good. It was clean well decorated and equipped with everything you need"
United States
Tom K.
The price is ￥15,103
￥42,356 total
includes taxes & fees
Aug 10 - Aug 11
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.
The price is ￥19,988
￥63,798 total
includes taxes & fees
Aug 11 - Aug 12
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
The price is ￥42,004
￥62,761 total
includes taxes & fees
Aug 11 - Aug 12
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.
The price is ￥21,970
￥74,166 total
includes taxes & fees
Aug 25 - Aug 26
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.
The price is ￥23,126
￥67,734 total
includes taxes & fees
Sep 2 - Sep 3
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
The price is ￥30,363
￥49,558 total
includes taxes & fees
Aug 31 - Sep 1
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.
The price is ￥26,430
￥80,712 total
includes taxes & fees
Aug 25 - Aug 26
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
The price is ￥20,153
￥45,631 total
includes taxes & fees
Aug 31 - Sep 1
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.
The price is ￥31,464
￥54,873 total
includes taxes & fees
Sep 1 - Sep 2
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.
The price is ￥35,303
￥53,228 total
includes taxes & fees
Aug 9 - Aug 10
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.
The price is ￥38,962
￥62,929 total
includes taxes & fees
Sep 4 - Sep 5
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.
The price is ￥32,226
￥77,423 total
includes taxes & fees
Aug 17 - Aug 18
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

Quality Inn & Suites South Portland

Quality Inn & Suites South Portland

10/10 Excellent
"Parking was a little tight for my car-width. Breakfast could have been a little hotter, but was generally good. There was a little dirt build-up at the room floor/wall intersection, but it was generally clean."
Peter 1-night trip
Posted 3 hours ago
Quality Inn & Suites South Portland

Find out more about Westbrook

Search for holiday rentals in Westbrook on Expedia! You can easily find your home rentals, villas, holiday apartments in Westbrook using one of the methods below:

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Look no further and take a look at our great range of rental properties in Westbrook!

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.