Holiday rentals in Westbrook

4.9 out of 5 average rating, 295 reviews

Loft in Portland

Large Loft—Walk to Breweries— Coffee Bar—King Bed

Located on outer Forest Avenue in Portland, Maine, Forest Loft is an impressive, custom built, 1 bedroom / 2 bathroom apartment with vaulted ceilings and plenty of space. Due to its close proximity to the breweries on Industrial Way, Forest Loft commonly welcomes craft beer fans from all over the world. Enjoy the proximity to popular amenities while only a short ride from downtown Portland. MAINE'S TOP HOST OF 2022 https://news.airbnb.com/celebrating-our-top-new-hosts-in-each-us-state-for-2022

4.9 out of 5 average rating, 229 reviews

Flat in Portland

Bright & Sunny Apartment with Patio

Centrally located in Portland, just steps away from USM/Maine Law, Back Bay, Bird & Co., Rose Foods, and other Oakdale gems. This apartment features personal touches and is stylishly furnished with attention to detail. Located on a quiet street in the Oakdale neighborhood, it is one of the best locations - as you can walk everywhere. It is a short Lyft or Uber to the famous Old Port. Feel the charm of a quiet neighborhood while also being close to city center. License #: STHR-004014-2022

4.93 out of 5 average rating, 237 reviews

Guest suite in Westbrook

Awesome open space in Westbrook near Portland, ME!

Welcome!! We're excited to share our house with you! You'll get the whole ground level of the house - two very large clean modern rooms with a private entrance, bathroom, and direct yard access to the hammock, fire pit, and wildlife. Off-street parking for 2 cars, kitchenette, 300Mbit wifi, smart TV, heat, ping pong, darts, and much more! 15 mins downtown Portland ($15 Uber) 1 mile from I-95 11 mins from the airport We will give you awesome tips on everything in the area and beyond!

4.97 out of 5 average rating, 214 reviews

Guest suite in Portland

Sunflower Retreat in North Back Cove

The Sunflower Retreat is a private, self-contained, peaceful hideaway. Located in the back half of an adorable 1920's home, this BnB space has everything you could need. A driveway leads you around to the back of the house, where a stone walkway guides you to your own private patio and entrance. A comfortable queen bed, kitchenette, full bathroom, closet, dining nook, black-out curtains, eatery, and television are included. Free street parking. Located in close proximity of many things!

4.96 out of 5 average rating, 157 reviews

Guest suite in Saco

LunaSea Suite

Be our guests and enjoy this dreamy, romantic little getaway and all that Saco and surrounding areas have to offer! Direct access to the River Walk. Short 5 minute walk to downtown Saco, Amtrak station, and 10 minute walk to downtown Biddeford. Visit our amazing shops, breweries, restaurants and cafes! Bayview Beach 3 miles OOB Pier 4.4 miles Private entrance and deck with outside fireplace. Hosts, Melissa and Doug, are quiet and considerate early risers with 2 friendly pups

4.99 out of 5 average rating, 138 reviews

Flat in Windham

The Roost - lovely one bedroom efficiency unit

Staying at the Roost means you will be 15 minutes to the ocean, the airport and to the Old Port; 10 minutes to nearby lakes and rivers; 5 minutes to everything downtown Westbrook has to offer, including many restaurants, parks, live music venues, shopping and a movie theater: what you are looking for is nearby! Kick back and relax in this calm, stylish space with a queen-sized bed, kitchenette, dining/work area, excellent wifi, a full bathroom and a big yard.

5 out of 5 average rating, 433 reviews

Barn in Portland

Garrison Cove Studio

Rare, Portland waterfront studio located in the heart of the historic Stroudwater neighborhood, awaits one or two guests looking for an urban hideaway. The newly created studio occupies a 150 year old post and beam barn situated on the banks of the Stroudwater and Fore Rivers. Enjoy morning coffee on the river swing, meditate to the soothing sound of the nearby waterfall or linger over your favorite glass of wine under the splendid backyard grape arbor.

4.94 out of 5 average rating, 72 reviews

Flat in Westbrook

Cozy King bed apt near Portland with free parking

Enjoy a comfortable and relaxing getaway in this charming second-floor studio, owned and operated by a local family. Nestled in a quiet neighborhood, yet just minutes from Downtown Portland with easy access to I-95 and I-295, it offers the perfect mix of peace and convenience. This cozy studio features a brand-new King bed with a fresh mattress and pillows, along with a 3/4 bath—perfect for unwinding after a day of exploring the city or coast.

4.92 out of 5 average rating, 282 reviews

Guest suite in East End

Gorgeous Studio 2 Blocks from Eastern Prom!

Located in Portland's trendy East End and within walking distance to the Old Port and Downtown, this beautiful studio is only 2 blocks from the Eastern Promenade and Casco Bay! You will have the Unit entirely to yourself with its own entrance, air conditioning, kitchenette, queen sized bed and an additional pull out single. Easily walk to all of the cool breweries, great restaurants, coffee shops, and night life! Welcome to Portland!

4.96 out of 5 average rating, 480 reviews

Tiny home in Portland

The Garden Cabin Tiny Home

Curious about tiny homes? Love dogs, gardens, pine trees, campfires, and birds? Hate cleaning fees? Our private 128 sqft cozy cabin is for you! On the spectrum between camping and a hotel room, it's a chill place to call home while visiting Portland. Enjoy our garden while sipping a beverage from your own deck or around the campfire. Heat and A/C when needed. Please, no smokers, kids under 13, or guest pets. STHR-000718-2018

4.9 out of 5 average rating, 198 reviews

Flat in Westbrook

Cozy 2 BR Apt in Walking Distance to Restaurants

This is a private two bedroom apartment in a great location (15 minutes to downtown Portland). The apartment is in walking distance to eateries, Riverbank Park, grocery stores and local breweries. It is also located across the street from the police station on a dead end street. The unit is child friendly and has a pack 'n Play and high chair. (Please note that linens are not provided for the Pack n’ Play.)

4.9 out of 5 average rating, 547 reviews

Home in Westbrook

Reno Barn w/ a lot of Charm! Breweries & Airport

** Cozy Renovated Barn w/ artist loft ** Minutes from airport and within walking distance to the Allagash Brewing Company & other breweries. Lots of hiking trails along the Presumpscot River. Short drive to downtown Portland, restaurants, music venues, beaches, lighthouses and nightlife. Barn is located in a quiet area ~ relax on the back deck with a glass of wine star gazing. Come check us out!!

Holiday rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Flats

Convenient locations with everyday essentials

Houses

A space that's all yours, with room for everyone

Popular amenities for Westbrook holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Westbrook

Private room in South Portland

5 out of 5 average rating, 72 reviews

Serene Wooded Oasis Near Portland & Beaches

LiliRating, 5 stars2 days ago

We loved Sarah’s home, it was super clean and had all the amenities we needed. Sarah also provided great local recommendations, which were very helpful. We visited a few of the places she suggested and even discovered a delicious Wild Maine blueberry ice cream spot nearby called Willard Scoop. Sarah was incredibly responsive to our questions, thank you again for the pen that night! We truly enjoyed our time in Maine and at her place. What we’ll miss most: giving pats to the handsome doodle 🐶😊. This was one of the most memorable trips we’ve had in Maine, and we’d definitely stay at Sarah’s place again if we come back to visit!

Private room in Westbrook

5 out of 5 average rating, 12 reviews

Cozy Vibes w/ 2 Rooms & Parking

LucyRating, 5 stars8 months ago

Adria’s place was really great! I think it is the perfect amount of space for a solo traveler or a couple. The location was peaceful and allowed me to relax after I went out, and it’s super easy to get to so I had no issues finding the place or getting Lyfts. There’s some restaurants and stores within a 20 minute walk and downtown Portland is like ~15 mins away. I felt like the location was really safe too. The place was super neat and organized so I didn’t have any issues finding anything I needed. Additionally, Adria was a really great host! She was kind and welcoming, and provided tons of recommendations and input. Plus her art is all over the place and it creates a really neat vibe. Barry was also the most chill dog ever.

4.89 out of 5 average rating, 626 reviews

Large, spacious, and eclectic Room, Private Bath

SaraRating, 5 stars2 days ago

We had a wonderful stay at Gail's place. Very peaceful and relaxing space. At Gail's suggestion we walked to a local noodle bar and had a fantastic dinner! Gail was warmly welcoming and helpful. We thoroughly enjoyed our stay with her!

4.87 out of 5 average rating, 240 reviews

Queen bedroom and private bath

DerrickRating, 5 stars2 weeks ago

It was a nice place to stay, being pretty close to the Deering High School and the downtown area. Very close to lots of fun! Josh was very chill and he knew lots about many restaurants, giving great suggestions 👍🏻

4.83 out of 5 average rating, 215 reviews

Rhoda Partridge House in Stroudwater Village

KipRating, 5 stars4 days ago

We were so happy to stay at John’s place. We had a very good night’s sleep. I only wish we could have stayed longer! Thank you for all your thoughtful amenities! Perhaps we’ll be lucky enough to meet you during some future stay! Grateful for your sharing your Historic Home! Kip Perkinson

4.88 out of 5 average rating, 735 reviews

Close to EVERYthing Portland + great neighborhood

RayRating, 5 stars2 days ago

A lovely little place perfect for a few nights stay! The hosts were wonderfully welcoming. We’d highly recommend to anyone passing through or staying for a night or two. The bed was comfortable with clean linens. The home was charmingly eclectic and had everything you need. Paul is a gem; don’t leave without having a conversation with him. Would stay again!

Hotel room in Downtown Portland

4.9 out of 5 average rating, 336 reviews

Black Elephant Hostel: bed in 8 bed MIXED dorm

ShannonRating, 5 stars3 weeks ago

Neat place. Very clean, and the staff are excellent. Great place to make friends and meet people if you’re traveling alone. It’s in a great location for getting around - plenty of restaurants and a good grocery store nearby, and the waterfront and pretty much anywhere else you’d want to see nearby are walkable.