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

Westbrook Holiday Rentals

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Our top choices for Westbrook holiday rentals

1. 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 NZ$744
includes taxes & fees
24 Aug - 25 Aug
Cozy 3BR | Pet Friendly | Near Portland | Parking

2. 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, (13 reviews)
"Fantastic property. Hosts were very communicative. Amazing stay. Great location! Thank you so much!"
United States
Laurie A.
Modern Apartment - 20 Mins to Portland, Deck, Grill & Firepit, King Bed, DogsOK

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

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

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 NZ$1,765
includes taxes & fees
24 Aug - 25 Aug
Sleeps 16+ | W/D | Parking | 15 mins to Old Port

5. Tranquility between the Lakes & Sea

Tranquility between the Lakes & Sea
Westbrook
The price is NZ$694
includes taxes & fees
8 Sept - 9 Sept
Tranquility between the Lakes & Sea

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 NZ$981
includes taxes & fees
18 Aug - 19 Aug
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres

7. 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 NZ$551
includes taxes & fees
24 Aug - 25 Aug
Peaceful 1BR | Reading Nook | Near Portland

8. 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 NZ$1,233
includes taxes & fees
31 Aug - 1 Sept
Evalina Hotel

9. The Weldon Hotel

The Weldon Hotel
4.5 star property
Downtown Portland
9.8 out of 10, Exceptional, (110 reviews)
"Really nice room and location"
United States
Victoria
The price is NZ$688
includes taxes & fees
1 Sept - 2 Sept
The Weldon Hotel

10. 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 NZ$673
includes taxes & fees
1 Sept - 2 Sept
Peaceful & minutes from the Old Port with private parking

11. Spacious 3 BR in Portland's Libbytown!

Spacious 3 BR in Portland's Libbytown!
Portland
9.4 out of 10, Exceptional, (55 reviews)
"Really cute, clean place that was a short drive to everything!"
United States
Annalise E.
The price is NZ$832
includes taxes & fees
31 Aug - 1 Sept
Spacious 3 BR in Portland's Libbytown!

12. 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, (24 reviews)
"Great place! We would definitely return if we were in the area."
United States
Preston
The price is NZ$555
includes taxes & fees
17 Sept - 18 Sept
Charming Studio apartment with WiFi, AC in welcoming Portland

13. Fortland Island Campground

Fortland Island Campground
1.0 star property
Portland
10.0 out of 10, Exceptional, (3 reviews)
"It was very quiet and liked the experience of staying in a camp like setting."
United States
leela srinivas
The price is NZ$857
includes taxes & fees
23 Aug - 24 Aug
Fortland Island Campground

14. Beautiful 1st Floor Apartment & Amazing Shower

Beautiful 1st Floor Apartment & Amazing Shower
Parkside
9.2 out of 10, Wonderful, (29 reviews)
"Apartment was as described. Clean, walking distort downtown and parks. Enjoyed stay. Easy communication with host. "
United States
James R.
The price is NZ$632
includes taxes & fees
30 Aug - 31 Aug
Beautiful 1st Floor Apartment & Amazing Shower

15. NEW 1 BDR-Heart of Munjoy Hill

NEW 1 BDR-Heart of Munjoy Hill
Munjoy Hill
9.8 out of 10, Exceptional, (7 reviews)
"Great location within walking distance to activities, food, the bay, etc. "
United States
Anne D.
The price is NZ$917
includes taxes & fees
18 Aug - 19 Aug
NEW 1 BDR-Heart of Munjoy Hill

16. 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 NZ$538
includes taxes & fees
1 Sept - 2 Sept
Sunny Spot with Private Parking.

17. 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 NZ$816
includes taxes & fees
9 Sept - 10 Sept
Furnished 1BR/1BA Walk to Maine Med/Mercy. Parking & All utilities included!

18. Adorable Portland getaway on the Eastern Promenade

Adorable Portland getaway on the Eastern Promenade
Munjoy Hill
9.6 out of 10, Exceptional, (140 reviews)
"Owner was so accommodating!"
United States
Kiernan
The price is NZ$527
includes taxes & fees
15 Sept - 16 Sept
Adorable Portland getaway on the Eastern Promenade

19. Ocean View East End Studio in a Historic Victorian

Ocean View East End Studio in a Historic Victorian
Portland
9.8 out of 10, Exceptional, (110 reviews)
"Lovely view and accessibility to the Old Port area. Enjoyed our relaxing stay! Thanks Dan! "
United States
David E.
The price is NZ$784
includes taxes & fees
23 Aug - 24 Aug
Ocean View East End Studio in a Historic Victorian

20. Stylish Brownstone Downtown Free St|Perfect Getaway for 2

Stylish Brownstone Downtown Free St|Perfect Getaway for 2
Downtown Portland
10.0 out of 10, Exceptional, (44 reviews)
"What a great stay! The rental property was absolutely fantastic! Can't wait to come back! Highly recommend staying here. "
United States
Ken C.
The price is NZ$1,160
includes taxes & fees
21 Aug - 22 Aug
Stylish Brownstone Downtown Free St|Perfect Getaway for 2
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

Find out more about Westbrook

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Westbrook holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Westbrook. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Westbrook. Seeing all the best attractions is bound to make you fall in love with Westbrook. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Westbrook short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Westbrook?

Yes, there are holiday rentals in Westbrook close to Westbrook Performing Arts Center, or you can select a more secluded option if you're looking for 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 coffee shops.

What are some of the best holiday rentals that Westbrook has to offer?

Quintessential Maine Beach Cottage: This holiday home rental outside of Westbrook is located on the beach, and has a private garden, a selection of games and a BBQ 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 that you can cook with friends or family.

How many holiday rentals will I find in Westbrook?

With 10 Expedia holiday rentals, you're guaranteed 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 wider area, you’ll find Westbrook Performing Arts Center and Maine Mall.

What’s a holiday rental in Westbrook like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Westbrook. Holiday rentals feature extras such as laundry facilities and kitchens so your stay will be comfortable. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from shared hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive option for small groups.