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
4 Sep - 6 Sep
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

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 AED 415
AED 1,297 total
includes taxes & fees
24 Aug - 25 Aug
Peaceful 1BR | Reading Nook | Near Portland
Interior

2. Tranquility between the Lakes & Sea

Tranquility between the Lakes & Sea
Westbrook
The price is AED 665
AED 1,509 total
includes taxes & fees
8 Sep - 9 Sep
Tranquility between the Lakes & Sea
TV, offices

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

Modern 3BR | W/D + Parking | Near Portland
Westbrook
The price is AED 573
AED 1,629 total
includes taxes & fees
23 Aug - 24 Aug
Modern 3BR | W/D + Parking | Near Portland
Dining

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

Sleeps 16+ | W/D | Parking | 15 mins to Old Port
Westbrook
The price is AED 1,506
AED 3,647 total
includes taxes & fees
24 Aug - 25 Aug
Sleeps 16+ | W/D | Parking | 15 mins to Old Port
Property grounds

5. 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 AED 1,484
AED 2,146 total
includes taxes & fees
24 Aug - 25 Aug
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres
3 bedrooms, premium bedding, iron/ironing board, travel crib

6. 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 AED 610
AED 1,674 total
includes taxes & fees
24 Aug - 25 Aug
Cozy 3BR | Pet Friendly | Near Portland | Parking
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, (14 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
The price is AED 405
AED 681 total
includes taxes & fees
1 Sep - 2 Sep
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
Sunny Spot with Private Parking.
Exterior detail

9. 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 AED 382
AED 945 total
includes taxes & fees
31 Aug - 1 Sep
1200 Sq Ft ♦ West End Gem ♦ Perfect Location
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 and very responsive host. I would definitely stay again when in Portland."
United States
Susan d.
The price is AED 413
AED 1,431 total
includes taxes & fees
3 Sep - 4 Sep
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
Outdoor dining

11. 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, (11 reviews)
"Cute, convenient spot!"
United States
Kelly S.
The price is AED 907
AED 1,473 total
includes taxes & fees
1 Sep - 2 Sep
Peaceful & minutes from the Old Port with private parking
Exterior detail

12. Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (141 reviews)
"Owner was so accommodating!"
United States
Kiernan
The price is AED 724
AED 1,153 total
includes taxes & fees
15 Sep - 16 Sep
Adorable Portland getaway on the Eastern Promenade
Front of property

13. Evalina Hotel

Evalina Hotel
2.5 star property
Downtown Portland
10.0 out of 10, Exceptional, (10 reviews)
"Truly a wonderful place with an unbeatable location. Highly recommend for a visit to Portland."
United States
Eric
The price is AED 1,903
AED 2,625 total
includes taxes & fees
31 Aug - 1 Sep
Evalina Hotel
Flat-screen TV, Netflix, books, streaming services

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

Walk to Old Port ♦ West End Condo ♦ Parking
West End
9.6 out of 10, Exceptional, (89 reviews)
"Host was very responsive, and helpful. Location is amazing for walking the city."
United States
Chris P.
The price is AED 417
AED 1,435 total
includes taxes & fees
2 Sep - 3 Sep
Walk to Old Port ♦ West End Condo ♦ Parking
Dining

15. 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
9.6 out of 10, Exceptional, (7 reviews)
"All was great...clean and convenient."
United States
Krista P.
The price is AED 749
AED 1,802 total
includes taxes & fees
9 Sep - 10 Sep
Furnished 1BR/1BA Walk to Maine Med/Mercy. Parking & All utilities included!
Property grounds

16. 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 AED 513
AED 1,736 total
includes taxes & fees
31 Aug - 1 Sep
Spacious and Contemporary Condo in the Heart of Portland - Close to Beach
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, (39 reviews)
"Absolutely wonderful little place to stay in Scarborough! "
United States
Eric S.
The price is AED 643
AED 1,169 total
includes taxes & fees
19 Sep - 20 Sep
Pine Point Beach private, quaint, charming studio.
Dining

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

Elegant condo - walk to Portland's best restaurants & Old Port
East Bayside
9.2 out of 10, Wonderful, (82 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.
The price is AED 617
AED 1,884 total
includes taxes & fees
25 Aug - 26 Aug
Elegant condo - walk to Portland's best restaurants & Old Port
Interior

19. 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, (25 reviews)
"Great place! We would definitely return if we were in the area."
United States
Preston
The price is AED 764
AED 1,225 total
includes taxes & fees
17 Sep - 18 Sep
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

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

10/10 Excellent
"Had an absolute wonderful stay"
Arlene 2-night trip
Posted 1 hour ago
Portland Regency Hotel & Spa

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.