Westbrook Vacation Rentals

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Our top choices for Westbrook vacation rentals

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 CA $621
CA $886 total
includes taxes & fees
May 25 - May 26
WINDABROOK Farm & Lodge - Recharge, Reset, Relax on 13 acres

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

Sleeps 16+ | W/D | Parking | 15 mins to Old Port
Westbrook
The price is CA $560
CA $1,265 total
includes taxes & fees
May 26 - May 27
Sleeps 16+ | W/D | Parking | 15 mins to Old Port

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, (8 reviews)
"Fantastic property. Hosts were very communicative. Amazing stay. Great location! Thank you so much!"
United States
Laurie A.
The price is CA $181
CA $559 total
includes taxes & fees
May 25 - May 26
Modern Apartment - 20 Mins to Portland, Deck, Grill & Firepit, King Bed, DogsOK

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

Modern 3BR | W/D + Parking | Near Portland
Westbrook
The price is CA $188
CA $544 total
includes taxes & fees
Jun 9 - Jun 10
Modern 3BR | W/D + Parking | Near Portland

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 CA $566
CA $617 total
includes taxes & fees
Jun 4 - Jun 5
Fortland Island Campground

Cozy Rock Cabin #thewaylifeshouldbe

Cozy Rock Cabin #thewaylifeshouldbe
Freeport
10.0 out of 10, Exceptional, (10 reviews)
"Very private property, was a great little retreat. Such a thoughtfully designed space, and loved being surrounded by nature, including breakfast with deer!"
United States
Dan M.
The price is CA $484
CA $860 total
includes taxes & fees
May 25 - May 26
Cozy Rock Cabin #thewaylifeshouldbe

Modern, Luxurious Cabin in the Woods - 03

Modern, Luxurious Cabin in the Woods - 03
Freeport
10.0 out of 10, Exceptional, (7 reviews)
"This was a perfect little cabin. It was clean, well equipped with a nice kitchen and bathroom, quiet and wooded location, and comfy bed. "
United States
Chris B.
The price is CA $251
CA $439 total
includes taxes & fees
May 25 - May 26
Modern, Luxurious Cabin in the Woods - 03

Clean cozy cottage 1 mile from beach.

Clean cozy cottage 1 mile from beach.
Old Orchard Beach
8.0 out of 10, Very good, (11 reviews)
"This house met all of our needs. It was updated and clean and has a nice little quiet enclosed back yard with a fire pit, grill and dining area. "
United States
Alyssa F.
The price is CA $303
CA $705 total
includes taxes & fees
May 25 - May 26
Clean cozy cottage 1 mile from beach.

3BR Coastal Gem with a 5 Min Drive to Ocean Fun

3BR Coastal Gem with a 5 Min Drive to Ocean Fun
Old Orchard Beach
10.0 out of 10, Exceptional, (7 reviews)
"The host was extremely responsive, the house perfectly accommodated our needs, and the beds were super comfortable. Highly recommend!"
United States
Tina B.
The price is CA $180
CA $527 total
includes taxes & fees
May 25 - May 26
3BR Coastal Gem with a 5 Min Drive to Ocean Fun

Mere Point Sunrise Views at Eastern Shore!

Mere Point Sunrise Views at Eastern Shore!
Brunswick
9.8 out of 10, Exceptional, (8 reviews)
"Lovely location "
United States
Michelle S.
The price is CA $420
CA $805 total
includes taxes & fees
May 26 - May 27
Mere Point Sunrise Views at Eastern Shore!

Large, luxurious geodesic dome - 04

Large, luxurious geodesic dome - 04
Freeport
10.0 out of 10, Exceptional, (3 reviews)
"Pet friendly and the experience is just amazing. Thank you for having us! "
United States
Rene B.
The price is CA $311
CA $530 total
includes taxes & fees
May 26 - May 27
Large, luxurious geodesic dome - 04

Pine Point Beach private, quaint, charming studio.

Pine Point Beach private, quaint, charming studio.
Blue Point
10.0 out of 10, Exceptional, (29 reviews)
"A great location to see Portland and surroundings. A very clean and nice place to stay. "
United States
Pam B.
The price is CA $224
CA $417 total
includes taxes & fees
May 30 - May 31
Pine Point Beach private, quaint, charming studio.

The Gregory House in Southern Maine close to many beaches & popular destinations

The Gregory House in Southern Maine close to many beaches & popular destinations
Downtown Saco
9.6 out of 10, Exceptional, (19 reviews)
"Lots to do. Great location"
United States
Bob Z.
The price is CA $578
CA $1,228 total
includes taxes & fees
May 25 - May 26
The Gregory House in Southern Maine close to many beaches & popular destinations

Gorgeous Downtown Townhome - Walk to Beach

Gorgeous Downtown Townhome - Walk to Beach
Old Orchard Beach
The price is CA $133
CA $596 total
includes taxes & fees
May 25 - May 26
Gorgeous Downtown Townhome - Walk to Beach

Serene Pine Point Escape — 1 Block to Beach, Marsh Views & Portland

Serene Pine Point Escape — 1 Block to Beach, Marsh Views & Portland
Pine Point
9.6 out of 10, Exceptional, (38 reviews)
"Cute place; clean and inviting. Would happily stay again!"
United States
Kelly M.
The price is CA $176
CA $478 total
includes taxes & fees
May 27 - May 28
Serene Pine Point Escape — 1 Block to Beach, Marsh Views & Portland

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)
"Great little place in south Portland! Close to many parks, lighthouses, and driving distance to downtown. Parking downtown and in the old port area can be tricky and expensive though. "
United States
Christopher R.
The price is CA $173
CA $345 total
includes taxes & fees
May 25 - May 26
Peaceful & minutes from the Old Port with private parking

The Bow Street Abode / Charming 2 BR Retreat

The Bow Street Abode / Charming 2 BR Retreat
Freeport
10.0 out of 10, Exceptional, (17 reviews)
"The property was clean and well kept and made for a lovely stay. "
United States
Carla Z.
The price is CA $345
CA $602 total
includes taxes & fees
Jun 8 - Jun 9
The Bow Street Abode / Charming 2 BR Retreat

A historic treasure in Southern Maine, very unique and spacious

A historic treasure in Southern Maine, very unique and spacious
Biddeford
10.0 out of 10, Exceptional, (44 reviews)
"Loved this house. Perfect for a getting ready spot for family before a wedding. Plently of rooms and space for parking "
United States
Jeanne C.
The price is CA $711
CA $1,393 total
includes taxes & fees
May 26 - May 27
A historic treasure in Southern Maine, very unique and spacious

Harborview - Curated East End Escape w/ Parking

Harborview - Curated East End Escape w/ Parking
Munjoy Hill
10.0 out of 10, Exceptional, (9 reviews)
"What a wonderful weekend in Portland Maine. The property was exceptional and in a great area. We felt comfortable and safe for our stay. We had a great time!"
United States
Kristyn E.
The price is CA $408
CA $732 total
includes taxes & fees
May 25 - May 26
Harborview - Curated East End Escape w/ Parking

Charming 1-bedroom ADU in wonderful Portland neighborhood

Charming 1-bedroom ADU in wonderful Portland neighborhood
Back Cove
The price is CA $242
CA $387 total
includes taxes & fees
May 25 - May 26
Charming 1-bedroom ADU in wonderful Portland neighborhood
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 vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

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?

The Lookout by Bayley Vacation Rentals: Visitors like this Westbrook vacation home rental. It is located by the ocean and has a patio, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals will I find in Westbrook?

With 8 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.