Westbrook Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Westbrook vacation rentals

10.0 out of 10, Exceptional, (1)
"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.
$289 nightly
The price is $315
Jan 7 - Jan 8, 2026
Total with taxes and fees
Peaceful 1BR | Reading Nook | Near Portland
10.0 out of 10, Exceptional, (6)
"Nice historic place, restored to all modern standards and amenities, while retaining its historical charm. "
United States
Aleksey I.
$418 nightly
The price is $456
Jan 1 - Jan 2, 2026
Total with taxes and fees
Modern Apartment - 20 Mins to Portland, Deck, Grill & Firepit, King Bed, DogsOK
$423 nightly
The price is $461
Jan 5 - Jan 6, 2026
Total with taxes and fees
Modern 3BR | W/D + Parking | Near Portland
2.0 star property
$981 nightly
The price is $1,069
Jan 5 - Jan 6, 2026
Total with taxes and fees
Sleeps 16+ | W/D | Parking | 15 mins to Old Port
10.0 out of 10, Exceptional, (12)
"We had a great stay here. It was very clean and conveniently located."
United States
Angela B.
$383 nightly
The price is $417
Jan 5 - Jan 6, 2026
Total with taxes and fees
Cozy 3BR | Pet Friendly | Near Portland | Parking
2.0 star property
10.0 out of 10, Exceptional, (24)
"Cozy, clean and comfortable! Perfect weekend beach get away! "
United States
jen e.
$183 nightly
The price is $199
Dec 28 - Dec 29
Total with taxes and fees
Pine Point Beach private, quaint, charming studio.
10.0 out of 10, Exceptional, (1)
$273 nightly
The price is $298
Dec 28 - Dec 29
Total with taxes and fees
Modern, luxurious cabin in the woods - 21

Apartment in Knightville

Sunny Spot with Private Parking.
2.0 star property
9.8 out of 10, Exceptional, (24)
"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
$184 nightly
The price is $201
Jan 4 - Jan 5, 2026
Total with taxes and fees
Sunny Spot with Private Parking.
9.6 out of 10, Exceptional, (127)
"Very convenient location. Comfortable accommodation! I would stay here again. "
United States
Cynthia W.
$149 nightly
The price is $162
Dec 28 - Dec 29
Total with taxes and fees
Adorable Portland getaway on the Eastern Promenade
10.0 out of 10, Exceptional, (3)
"The location was wonderful! The host was so communicative and kind!"
United States
Courtney W.
$179 nightly
The price is $195
Jan 4 - Jan 5, 2026
Total with taxes and fees
Adorable 1 bedroom cabin only 50 ft from beach#1

Apartment in West Bayside

In-town no frills 2 bedroom apt
8.6 out of 10, Excellent, (16)
"Good place to stay in. Safe. However, it would be good to know about the steep and narrow spiral staircase, in case you have lots of heavy luggage."
United States
Omar S.
$154 nightly
The price is $156
Jan 1 - Jan 2, 2026
Total with taxes and fees
In-town no frills 2 bedroom apt
8.0 out of 10, Very Good, (24)
"Was the perfect place to unwind. Close enough to walk to beach, restaurants and shops. Enjoyed our stay emensly!"
United States
Maria H.
$195 nightly
The price is $213
Jan 5 - Jan 6, 2026
Total with taxes and fees
Updated 2 BD cottage. 10 min walk to Pier & Beach sleeps 5
9.8 out of 10, Exceptional, (7)
"This well- appointed apartment was perfect for our stay in the Portland area. Jennifer was always quick to answer any questions. We would definitely recommend this listing."
United States
Lynn E.
$197 nightly
The price is $215
Jan 4 - Jan 5, 2026
Total with taxes and fees
Peaceful & minutes from the Old Port with private parking
8.4 out of 10, Very Good, (7)
"The summary and the pictures shown are exactly what you’re going to get. The owner did a good job with the description, I "
United States
Alexandria T.
$133 nightly
The price is $135
Dec 29 - Dec 30
Total with taxes and fees
Studio Apartment near downtown Walkable!

Vacation Home in Harpswell

Orchid Harbor, Bailey Island 3BR
9.8 out of 10, Exceptional, (8)
"Orchid Harbor was perfect for my 3 week escape from life. Bailey Island is quiet and the house is comfortable and accommodating for family and friends.The outdoor seating along the ocean was our favorite place to be."
United States
Karen T.
$492 nightly
The price is $498
Jan 1 - Jan 2, 2026
Total with taxes and fees
Orchid Harbor, Bailey Island 3BR
9.0 out of 10, Wonderful, (26)
"This was a clean and good location for our stay. "
United States
Jocelyn R.
$145 nightly
The price is $158
Jan 4 - Jan 5, 2026
Total with taxes and fees
Beautiful 1st Floor Apartment & Amazing Shower
2.0 star property
10.0 out of 10, Exceptional, (4)
"Host was very welcoming and check in was simple "
United States
Michael C.
$124 nightly
The price is $135
Dec 30 - Dec 31
Total with taxes and fees
Spacious Studio Near Sebago Lake
9.8 out of 10, Exceptional, (52)
"Great location and cozy."
United States
Heather G.
$208 nightly
The price is $227
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cozy, Elegant and Bright 2 bed in the East End
9.6 out of 10, Exceptional, (11)
"A great location and a comfortable place to stay!"
United States
Andrew K.
$197 nightly
The price is $214
Dec 29 - Dec 30
Total with taxes and fees
Charming Studio apartment with WiFi, AC in welcoming Portland
10.0 out of 10, Exceptional, (3)
" The place was wonderful!! Very peaceful and beautiful!! "
United States
Anonymous traveler
$619 nightly
The price is $682
Jan 5 - Jan 6, 2026
Total with taxes and fees
Waterfront Access with Kayaks, Private Deck and a Firepit
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Westbrook Hotel Reviews

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 $140 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.

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?

Private, 2nd Floor Cottage with Wonderful Ocean Views- Perfect for Families! : You might want to consider this vacation home rental near Westbrook, which is located in the city center and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of books.

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.