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Westbrook Vacation Rentals

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Check prices for these dates

Tonight
Dec 13 - Dec 14
Tomorrow
Dec 14 - Dec 15
Next weekend
Dec 19 - Dec 21
In two weeks
Dec 26 - Dec 28

Our top choices for Westbrook vacation rentals

Deluxe Suite, 1 King Bed | Private kitchen | Full-size fridge, microwave, oven, stovetop
The Weldon Hotel

Aparthotel in Downtown Portland

The Weldon Hotel
4.5 star property
9.8 out of 10, Exceptional, (89)
"Loved this place and would definitely stay here next time we go back."
United States
Eleni
The price is ￥28,747
￥54,706 total
includes taxes & fees
Jan 5 - Jan 6, 2026
The Weldon Hotel
On the beach, sun loungers, beach towels
Quintessential Maine Beach Cottage

Vacation Home in Goose Rocks Beach

Quintessential Maine Beach Cottage
9.8 out of 10, Exceptional, (138)
"Absolutely beautiful surroundings and cozy place made for an unforgettable experience! "
United States
Sara S.
Quintessential Maine Beach Cottage
Beach nearby
Perfect for Families & friends re-unions! Outdoor Hot Tub, 50 yards to the beach!

Vacation Home in Old Orchard Beach

Perfect for Families & friends re-unions! Outdoor Hot Tub, 50 yards to the beach!
9.8 out of 10, Exceptional, (97)
"The location was perfect and the house was exceptional. The host and property manager were very responsive and helpful. Would definitely recommend a stay!"
United States
Kathleen C.
The price is ￥93,330
￥193,779 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Perfect for Families & friends re-unions! Outdoor Hot Tub, 50 yards to the beach!
Beach
Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!

Vacation Home in Old Orchard Beach

Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!
9.8 out of 10, Exceptional, (45)
"Excellent family stay. Backyard is nice and shaded, you can see the ocean from the house and amenities are great. "
United States
Danielle N.
Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families!
Outdoor dining
Sebago Lake Cottage on Raymond Cape

Cabin in Raymond

Sebago Lake Cottage on Raymond Cape
10.0 out of 10, Exceptional, (48)
"We loved this cabin! A stone throw from the lake. Private and quiet. "
United States
Kathy K.
Sebago Lake Cottage on Raymond Cape
On the beach
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

Vacation Home in Bailey Island

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
10.0 out of 10, Exceptional, (234)
"Tremendous stay, great property and host."
United States
Curtis G.
New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
On the beach
Sensational Beachfront Property Old Orchard Beach, with indoor elevator

Vacation Home in Old Orchard Beach

Sensational Beachfront Property Old Orchard Beach, with indoor elevator
9.6 out of 10, Exceptional, (67)
"In one word AMAZING! We rented this property to gather our immediate family, adult children and grandchildren. We had a tragedy in our family as my oldest son was killed, this made our once close family, split apart. This property was so beautiful and such a happy place to be that my prayers were answered my family began the healing process. The location and the views one could not be unhappy. Thank you Jason for helping to make the stay amazing!"
United States
Helen F.
The price is ￥108,911
￥212,970 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Sensational Beachfront Property Old Orchard Beach, with indoor elevator
Beach nearby
The Moonglow! A beautiful ocean view house in Biddeford!

Vacation Home in Biddeford

The Moonglow! A beautiful ocean view house in Biddeford!
9.8 out of 10, Exceptional, (128)
"Beautiful place "
United States
Robert D.
The Moonglow! A beautiful ocean view house in Biddeford!
Terrace/patio
1 room luxury ocean front studio cottage

Apartment in Harpswell

1 room luxury ocean front studio cottage
9.6 out of 10, Exceptional, (171)
"Very clean beautiful view we definitely enjoyed ourselves "
United States
Ilona F.
1 room luxury ocean front studio cottage
Terrace/patio
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough

Vacation Home in Grand Beach

Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough
2.0 star property
9.0 out of 10, Wonderful, (17)
"Incredibly wonderful beach house. Plenty of room for 8 adults, 6 children. Would recommend for any group with lots of ages and preferences. Helped to create wonderful family reunion."
United States
Ina-Lee B.
Spacious 7-bedroom house with WiFi and AC in fabulous Pine Point Scarborough
Interior
Charming Studio apartment with WiFi, AC in welcoming Portland

Apartment in Munjoy Hill

Charming Studio apartment with WiFi, AC in welcoming Portland
9.6 out of 10, Exceptional, (11)
"A great location and a comfortable place to stay!"
United States
Andrew K.
The price is ￥17,493
￥32,966 total
includes taxes & fees
Dec 14 - Dec 15
Charming Studio apartment with WiFi, AC in welcoming Portland
TV
Private Entrance Residential Portland

Apartment in Deering Center

Private Entrance Residential Portland
9.2 out of 10, Wonderful, (5)
"Check in was simple. Quaint place. "
United States
Danielle C.
Private Entrance Residential Portland
1 bedroom, bed sheets
Studio Unit Walkable Everywhere

Apartment in West Bayside

Studio Unit Walkable Everywhere
5.8 out of 10, (7)
"We didn't stay there at all. Canceled reservation "
United States
Dianne
The price is ￥10,612
￥21,776 total
includes taxes & fees
Dec 14 - Dec 15
Studio Unit Walkable Everywhere
TV, DVD player, books
Charming cottage with outdoor space, full kitchen, & WiFi - near beach

Vacation Home in Goose Rocks Beach

Charming cottage with outdoor space, full kitchen, & WiFi - near beach
9.4 out of 10, Exceptional, (34)
"Perfect location for our family vacation "
United States
Nancy O.
Charming cottage with outdoor space, full kitchen, & WiFi - near beach
Smart TV
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC

Cabin in Old Orchard Beach

Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC
9.8 out of 10, Exceptional, (12)
"Walking distance to the board walk. Clean and just enough space for 4 of us. Had everything we needed plus plenty of towels! "
United States
Natalia R.
Charming 2-Bedroom Cottage in Peaceful Old Orchard Beach with WiFi, AC
Outdoor dining
THE LILLIPAD.Off-grid A frame. Sebago lake region!

Cabin in Standish

THE LILLIPAD.Off-grid A frame. Sebago lake region!
9.8 out of 10, Exceptional, (7)
"Great view of the pond and nice accommodations for a single guest."
United States
Brian M.
THE LILLIPAD.Off-grid A frame. Sebago lake region!
Interior
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach

Cottage in Old Orchard Beach

Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
9.8 out of 10, Exceptional, (65)
"Nice spot to stay with our pup! Chris was available and helpful, and it’s clear he takes care of his property. "
United States
John and Lori W.
Dog Friendly, Relaxing Cottage Stay • Steps Away from The Beach
Fridge, oven, stovetop, coffee/tea maker
Updated Long Island Maine Cottage

Cottage in Long Island

Updated Long Island Maine Cottage
10.0 out of 10, Exceptional, (7)
"Great island house! Loved how stocked the kitchen was, we had comfortable beds and even beach chairs and cooler. We would definitely stay here again. "
United States
Serra C.
Updated Long Island Maine Cottage
Property grounds
Spectacular Beachfront Condo-Watch sunrise from deck overlooking beach.

Condo in Old Orchard Beach

Spectacular Beachfront Condo-Watch sunrise from deck overlooking beach.
9.8 out of 10, Exceptional, (36)
"Great spot...everything was great "
United States
Frank R.
Spectacular Beachfront Condo-Watch sunrise from deck overlooking beach.
Interior
Back yard paradise

Vacation Home in Portland

Back yard paradise
9.8 out of 10, Exceptional, (22)
"Excellent home overall! Great equipment, great kitchen, great pool, nice patio! Easy access to the home and driveway! Probably the best house I’ve stayed in ! "
United States
Justin J.
Back yard paradise
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
"Perfect location, great hospitality. "
Sebastian 2-night trip
Posted 1 day ago
Portland Regency Hotel & Spa

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:

  • View our selection of featured holiday rentals in Westbrook
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  • Enter your travel dates to view the best deals on holiday rentals in Westbrook while they last

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 Happy Wheels Skate 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 9 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 Maine Mall and University of New England.

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.