Westbrook holiday rentals

We found 493 holiday rentals — enter your dates for availability
Discover a selection of 10 homes and other holiday rentals in Westbrook that are perfect for your trip. Whether you're staying in a holiday rental with a group or just with your pet, you'll have the best amenities for spending time at your home away from home, which might include Wi-Fi and a washer and dryer. You're sure to find a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Westbrook

Showing deals for:18 Dec - 25 Dec

Exterior
Living area
Private kitchen
Dining
Exceptional
(21 reviews)

Entire House - three suites - conferences, reunions, retreats

Westbrook

8% off
AU$10,974
for 7 nights, 1 home
AU$1,568 per night
includes taxes & fees
Entire House - three suites - conferences, reunions, retreats
Back yard
Willard Beach
Living area
Dining
Exceptional
(72 reviews)

Willard Beach Neighborhood-Close to all Southern Maine has to offer!

South Portland

8% off
AU$4,375
for 7 nights, 1 home
AU$625 per night
includes taxes & fees
Willard Beach Neighborhood-Close to all Southern Maine has to offer!
Private kitchen
Outdoor dining
The living room leads out to a private deck with a dining table that seats 4.
Exterior detail
Exceptional
(43 reviews)

Modern & Sunny House Steps from the Promenade.

Portland

8% off
AU$3,913
for 7 nights, 1 home
AU$559 per night
includes taxes & fees
Modern & Sunny House Steps from the Promenade.
Living area
Marina
Living area
Private kitchen
Exceptional
(13 reviews)

Renovated Apartment in Willard Square Area of South Portland, Maine.

South Portland

16% off
AU$2,547
for 7 nights, 1 apartment
AU$364 per night
includes taxes & fees
Renovated Apartment in Willard Square Area of South Portland, Maine.
Private kitchen
Living area
Dining
Interior
Exceptional
(134 reviews)

Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants

Portland

12% off
AU$2,935
for 7 nights, 1 apartment
AU$419 per night
includes taxes & fees
Whether With Family or Friends Shop, Sight See & Dine at Great Restaurants
View from inside unit.
Large open concept living space with tall sloped celling and a loft.
Lobby can be accessed from Patton Ct or Exchange St. Door code will be provided.
Oven, Keurig, microwave, fridge, toaster, and dishwasher.
Exceptional
(7 reviews)

Exchange Street Skylight Loft

Portland

8% off
AU$3,888
for 7 nights, 1 apartment
AU$555 per night
includes taxes & fees
Exchange Street Skylight Loft
Space for shoes and coats before going upstairs into the living space.
Walk around behind the garage to access the apartment.
Room
Private kitchen
Exceptional
(16 reviews)

Private studio nestled in woods outside Portland

Westbrook

13% off
AU$2,172
for 7 nights, 1 apartment
AU$310 per night
includes taxes & fees
Private studio nestled in woods outside Portland
Room
Living area
Private kitchen
Off-street parking behind building dedicated to this unit only.
Exceptional
(41 reviews)

Eastbayside/Munjoy - Charming Downtown Escape

Portland

8% off
AU$2,681
for 7 nights, 1 apartment
AU$383 per night
includes taxes & fees
Eastbayside/Munjoy - Charming Downtown Escape
Private kitchen
Outdoor dining
Dining
Interior
Exceptional
(13 reviews)

Peaceful & minutes from the Old Port with private parking

South Portland

8% off
AU$2,197
for 7 nights, 1 apartment
AU$314 per night
includes taxes & fees
Peaceful & minutes from the Old Port with private parking
Private kitchen
Coziest place to relax and unwind have a fire and enjoy the fall and winter
Living area
Exterior
Exceptional
(68 reviews)

Clean, Cozy, and Professional Waterfront Home- minutes to Portland

Falmouth

8% off
AU$6,497
for 7 nights, 1 home
AU$928 per night
includes taxes & fees
Clean, Cozy, and Professional Waterfront Home- minutes to Portland
Private kitchen
Dining
Interior
Outdoor dining
Exceptional
(147 reviews)

Fall In Love With Portland!

Portland

8% off
AU$2,706
for 7 nights, 1 apartment
AU$387 per night
includes taxes & fees
Fall In Love With Portland!
Living area
Interior
Exterior detail
Living area
Exceptional
(100 reviews)

2 Bedroom Apartment Unit In Portland's Historic West End Neighborhood

Portland

8% off
AU$2,834
for 7 nights, 1 apartment
AU$405 per night
includes taxes & fees
2 Bedroom Apartment Unit In Portland's Historic West End Neighborhood
Scales! The best spot in town for a delish dinner.
Tour the Victorian Mansion at the bottom of the street.
Interior
Pocket doors pull out from the walls separating the livingroom and bedroom.
Exceptional
(63 reviews)

Historic Home in the West End. Private Parking.

Portland

8% off
AU$2,519
for 7 nights, 1 apartment
AU$360 per night
includes taxes & fees
Historic Home in the West End. Private Parking.
Pia Men Miyake, the best place for lunch!
Smalls! A short walk from the house.
Room
Dining
Exceptional
(23 reviews)

West End Bright Spot with Parking.

Portland

8% off
AU$2,038
for 7 nights, 1 apartment
AU$291 per night
includes taxes & fees
West End Bright Spot with Parking.
Exterior detail
Interior
Property grounds
Dining
Exceptional
(21 reviews)

New England Charm, Portland - Parking included

Portland

8% off
AU$4,262
for 7 nights, 1 apartment
AU$609 per night
includes taxes & fees
New England Charm, Portland - Parking included
Festive lighting at your control.
5 min car ride to Downtown/Old Port.
Mix of nautical and rustic elements throughout.
Large, well-stocked Kitchen w/stainless steel counter and appliances
Exceptional
(131 reviews)

City Amenities, Casco Bay Sunrises and Natural Beauty

Portland

8% off
AU$2,995
for 7 nights, 1 apartment
AU$428 per night
includes taxes & fees
City Amenities, Casco Bay Sunrises and Natural Beauty
Interior
Interior
Room
Walnut topped kitchenette counter with coffee maker.
Exceptional
(43 reviews)

Fresh East End Apartment Walkable to Downtown Portland

Portland

8% off
AU$4,200
for 7 nights, 1 apartment
AU$600 per night
includes taxes & fees
Fresh East End Apartment Walkable to Downtown Portland
Room
Private kitchen
Dining
Living area
Exceptional
(14 reviews)

Harborview - Curated East End Escape w/ Parking

Portland

8% off
AU$7,251
for 7 nights, 1 apartment
AU$1,036 per night
includes taxes & fees
Harborview - Curated East End Escape w/ Parking
Living area
Interior
Interior
Dining
Exceptional
(22 reviews)

West End's Diamond in the Rough 2-bedroom Apartment with Parking & WiFi

Portland

8% off
AU$4,417
for 7 nights, 1 apartment
AU$631 per night
includes taxes & fees
West End's Diamond in the Rough 2-bedroom Apartment with Parking & WiFi
Discover Victoria Mansion at the bottom of the street.
Scales in the Old Port for the best seafood
Room
The State Theater is a 5 minute walk away.
Exceptional
(55 reviews)

Charming West End Hideaway. Private Parking

Portland

8% off
AU$2,704
for 7 nights, 1 apartment
AU$386 per night
includes taxes & fees
Charming West End Hideaway. Private Parking

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    More space, more privacy, more amenities — more value

Explore the riverfront setting in Westbrook

The riverfront and surrounding scenery provide a peaceful ambience to your holiday home in Westbrook. Travellers to this welcoming city praise the shopping, restaurants and spas. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in and around Westbrook

Are you searching for top things to see and do while you're in town? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that Westbrook has to offer. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Aquaboggan Water Park (8.8 mi / 14.2 km)
  • Dunegrass Golf Club (10.6 mi / 17 km)
  • Funtown Splashtown USA (10.7 mi / 17.3 km)
  • Pirate's Cove (11.4 mi / 18.3 km)
  • Old Orchard Beach Parasail (14.8 mi / 23.8 km)
  • Point Sebago Golf Resort (19 mi / 30.5 km)

Exploring the natural features in Westbrook

Whether you're an active traveller or just want to spend some time taking in the scenery, Westbrook is a great place to get outside. Here are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • Thompson's Point (4.4 mi / 7.1 km)
  • Eastern Promenade (6.5 mi / 10.4 km)
  • East End Beach (6.6 mi / 10.6 km)
  • Willard Beach (7.5 mi / 12.1 km)
  • Sand Beach (8 mi / 12.9 km)
  • Higgins Beach (9.3 mi / 15 km)

Transport options to and around Westbrook

Fly into Portland, ME (PWM-Portland Intl. Jetport), the closest airport, located 3.6 mi (5.9 km) from the city centre. If you can't find a flight that's convenient for your trip, you could also fly into Sanford, ME (SFM-Sanford Seacoast Regional), which is 25.5 mi (41.1 km) away.

Frequently asked questions

Where are the best areas for renting a beach house in Westbrook?
For renting a beach house in Westbrook, consider the picturesque coastline along the Saco River and its proximity to nearby beaches. The area around Ferry Beach State Park offers holiday rentals that provide easy access to sandy shores and beautiful natural scenery. Many of the properties here feature amenities such as spacious outdoor decks, private gardens, and fully equipped kitchens, making them ideal for families or groups seeking a relaxing coastal getaway.Additionally, the nearby town of Scarborough, just a short drive away, boasts stunning beaches like Scarborough Beach and Higgins Beach. Rentals in this area often come with added luxuries such as outdoor showers for rinsing off after a day at the beach, as well as proximity to local seafood restaurants and shops that enhance the seaside experience. Properties here may also include communal pool access and fitness facilities, suiting those looking for a more active holiday.For those interested in outdoor activities, the surrounding region offers opportunities for kayaking, paddleboarding, and hiking along scenic trails.
Where are the best Westbrook ski resort rentals?
For ski resort rentals near Westbrook, Maine, the closest skiing options are found at nearby resorts such as Shawnee Peak and Sunday River. In the vicinity of Shawnee Peak, travellers can seek accommodations in towns like Bridgton, where a range of properties from cosy cabins to larger family homes are available. These rentals often feature amenities such as fireplaces, fully equipped kitchens, and outdoor decks, providing a comfortable base for relaxation after a day on the slopes.Further afield, Sunday River, situated in Newry, offers a variety of rental options, including ski-in/ski-out lodges and chalets, great for those looking to maximise their ski time. Many of these properties come with amenities like hot tubs, ski storage, and spacious living areas, ideal for gathering after a long day of skiing. The area also has local shops and dining options, enhancing the overall experience for visitors.Additionally, Westbrook itself is a charming town with access to outdoor activities and beautiful landscapes, making it a great choice for those who want a blend of skiing and local culture. Properties in this area may include modern apartments or traditional New England homes, often equipped with conveniences such as Wi-Fi, laundry facilities, and proximity to parks and recreational areas.
What is the most popular type of holiday rental accomodation in Westbrook?
In Westbrook, holiday houses are the most popular type of holiday rental, with about 36 available throughout the area. These properties provide ample space, making them ideal for families or groups, and typically include multiple bedrooms, fully equipped kitchens, and outdoor areas for relaxation. Many of these houses are situated in peaceful neighbourhoods, offering a serene environment for visitors. Additionally, there are around 20 apartments available, which are often found closer to local amenities and attractions. These apartments generally feature cosy living spaces and kitchen facilities, suiting those looking for a more compact stay while still enjoying the comforts of home.
Are there any family house rentals in Westbrook?
In Westbrook, Maine, there are several family-friendly house rentals available, with around 11 options for visitors to choose from. The city is known for its charming neighbourhoods and easy access to outdoor activities, making it a great spot for families. Many of these homes offer spacious living areas, fully equipped kitchens for preparing meals, and outdoor spaces where children can play and explore.Proximity to local parks, such as the picturesque Riverbank Park, provides families with ample opportunities for picnics and recreational activities. Additionally, the nearby Presumpscot River is superb for kayaking and fishing, allowing adventurous families to enjoy nature together.
Can I rent a holiday home with a pool or hot tub in Westbrook?
In Westbrook, Maine, there are several holiday homes available for rent that come with pools or hot tubs. This charming town provides a peaceful retreat while still being conveniently located near the vibrant city of Portland. Many of the properties feature private outdoor pools, hot tubs, and spacious patios, great for relaxing after a day of exploring.Travellers can expect amenities such as fully equipped kitchens for self-catering, comfortable living areas, and sometimes even access to outdoor grills, making it an ideal setting for family gatherings or special occasions. Westbrook's scenic surroundings, including parks and rivers, add to the appeal, providing opportunities for outdoor activities and relaxation.
Are there pet-friendly house rentals in Westbrook?
In Westbrook, Maine, there are several pet-friendly house rentals available for those looking to enjoy a stay with their furry companions. Many of these properties offer convenient amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces where pets can play.The rentals are typically situated near local parks and green spaces, providing ample opportunities for walks and outdoor activities. Additionally, the vibrant downtown area is within reach, where visitors can explore charming shops and restaurants, some of which welcome pets.
Are there any remote work holiday rentals in Westbrook?
In Westbrook, Maine, there are numerous options for remote work holiday rentals, with around 48 properties available. This charming city, located just a short drive from Portland, offers a variety of accommodations suited for those looking to combine work and leisure. Many of these rentals come equipped with essential amenities such as free Wi-Fi and dedicated workspaces, ensuring a productive environment for remote workers.Travellers can find properties ranging from modern apartments to spacious homes, often featuring comfortable living areas, fully equipped kitchens, and outdoor spaces for relaxation after a day of work. The local area provides a pleasant backdrop, with scenic parks, walking trails, and easy access to the vibrant dining and shopping scene in nearby Portland. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Westbrook?
In Westbrook, popular rental amenities include fully equipped kitchens, allowing guests to prepare their own meals and enjoy the convenience of home cooking. Most rentals also come with a coffee and tea maker, superb for brewing a warm drink at any time. Many properties feature a deck or patio, providing outdoor space for relaxation and enjoying the fresh air. Additionally, some rentals include blenders, which are great for making smoothies or other beverages. Onsite parking is commonly available, ensuring easy access for guests travelling by car.
When is the best time to visit Westbrook for a holiday rental?
The best time to visit Westbrook, Maine, for a holiday rental is during the peak season from January to March. This period attracts winter enthusiasts eager to enjoy the snowy landscapes and a variety of outdoor activities. With temperatures typically ranging from -6 to 4 degrees Celsius, visitors can partake in skiing, snowshoeing, and ice skating, all while soaking in the charming winter atmosphere that Westbrook has to offer.January stands out as the most popular month, providing a vibrant winter experience. The town comes alive with seasonal festivities and opportunities for cosy evenings by the fire after a day spent exploring the picturesque surroundings. The snowy scenery creates a beautiful backdrop for both outdoor adventures and indoor relaxation.For those seeking a more budget-friendly trip, consider visiting in November. This month allows for a quieter experience while enjoying the beautiful autumn leaves and the crisp air before winter sets in. You can explore the local parks and trails at a leisurely pace, making it a superb time for nature walks and enjoying the serene atmosphere.
What are the top attractions in Westbrook?
In Westbrook, Maine, visitors can explore several great attractions that highlight the area's charm and natural beauty. The Presumpscot River, which runs through the city, offers scenic views and opportunities for kayaking and fishing. One of the key attractions is the Riverwalk, a lovely area for walking and enjoying the riverside scenery, complete with parks and picnic spots.For those interested in history, the Westbrook Historical Society showcases the city's rich heritage, while the nearby Saccarappa Falls offers an impressive natural sight. The area is also home to several local breweries and restaurants that feature farm-to-table cuisine, enhancing the culinary experience.Nature enthusiasts can venture to the nearby Sebago Lake State Park, which is just a short drive away, offering hiking trails, swimming areas, and campgrounds.
Are all fees included in the Westbrook holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Westbrook holiday homes with parking?
Stayz offers a wide selection of holiday homes in Westbrook with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Westbrook holiday homes?
You can find great discounts on holiday homes in Westbrook on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Westbrook holiday home booking on Stayz?
To find Westbrook holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Westbrook?
A long-stay holiday home in Westbrook is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Westbrook holiday home?
Book your Westbrook holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Westbrook?
Prices for holiday homes in Westbrook vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Westbrook to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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