A Travel Price Comparison for United States of America Winston-Salem vs. Kennebunkport for Food, Families, Couples, and Attractions

Should you visit Winston-Salem or Kennebunkport?

Which is cheaper to visit? Which is more expensive for vacation?

Should I visit Winston-Salem or Kennebunkport? This is a common question asked by many travelers. By figuring out which city has activities that align with your interests along with knowing which is more affordable, you'll understand where you can get more bang for your buck. So, let's dive into the details and the data, which all comes from actual travelers.

Winston-Salem

Winston-Salem is a under-rated, welcoming, and friendly city. Other reasons to visit include museums, nightlife, and food.

Kennebunkport

Kennebunkport is a character-filled, charming, and quaint town. This is a great small town that is just waiting to be explored. It offers plenty of beauty for visitors. Other popular activities here include hiking, shopping, and museums.

Winston-Salem and Kennebunkport: Pros and Cons

Pros
  • Popular museums and historical sights
  • Active nightlife
  • Scenic old town
  • Family-friendly
  • Good for students
Things to Consider
  • Less popular with couples
Pros
  • Popular museums and historical sights
  • Active nightlife
  • Nice resorts
  • Good for hiking
  • Family-friendly
  • Good for couples and romance
  • Small town charm


Is there more to do in Winston-Salem or Kennebunkport?

Visitors will usually find more to do in Kennebunkport than Winston-Salem, as it offers more sights, attractions, and activities. Kennebunkport is better known for its food, resorts, hiking, shopping, small town charm, and impressive beauty, while Winston-Salem is more popular for its historical sights. Kennebunkport is more touristy than Winston-Salem and is popular for its historic and charming atmosphere, its wonderful local seafood, and its stunning coastline. Also, Kennebunkport is famous for Dock Square. Winston-Salem is well known for it's southern character and quaint college campuses.

How is Winston-Salem different from Kennebunkport?

Which is Better for a Holiday?

Let's take a look at the differences and similarities between Kennebunkport and Winston-Salem. Then, you can decide for yourself which place is better for your next trip.

Are the Museums and Historical Sights Better in Winston-Salem or Kennebunkport?

Winston-Salem
Kennebunkport

For an educational experience, head to a museum or a notable sight in either Winston-Salem or Kennebunkport.

If you're looking for an educational opportunity, there are a decent number of museums and historical sights around Winston-Salem. Old Salem has a nice concentration of museums and gardens. Outside of the old town you'll find several art museums like the Museum of Early Southern Decorative Arts and the Reynolda House Museum of American Art.

Kennebunkport is a good place to visit if you're interested in museums or other recognizable sights. There are a handful of local museums around town like the Brick Store Museum, the First Families Kennebunkport Museum, and the Seashore Trolley Museum.


Is the Food Better in Winston-Salem or Kennebunkport? Which Destination has the Best Restaurants?

Winston-Salem
Kennebunkport

Kennebunkport is notable for its local cuisine and restaurants. Also, Winston-Salem is not as famous, but is still a good city to visit for its restaurants.

Dining out in Kennebunkport is an experience not to be missed. Fine dining, seafood restaurants, and local cafes all make this a wonderful town for foodies. The town's famous for its lobster, but you can also try the scallops, crab, or oysters.

There are plenty of up and coming restaurants around Winston-Salem. North Carolina barbecue is popular around town. The city is also the birthplace of Krispy Kreme donuts and during the holiday season you should sample the local Moravian Cookies.

Is Winston-Salem or Kennebunkport Better for Nightlife?

Winston-Salem
Kennebunkport

Evening events are notable in both Winston-Salem and Kennebunkport.

There's a variety of activities in the evening in Winston-Salem. Local breweries are popping up around town. You'll also find active nightlife venues near the colleges and universities.

With a handful of venues, visitors can find a fairly lively vibe in Kennebunkport. You can check out the happy hours that many of the bars in the waterfront area host regularly.

Is Winston-Salem or Kennebunkport Better for Resorts?

Winston-Salem
Kennebunkport

Kennebunkport is notable for its resorts. However, Winston-Salem is not a resort destination.

Kennebunkport is known as a popular and fun resort destination. Luxury resorts and classic inns provide traditional and local accommodation options for visitors.

Winston-Salem is not a resort destination.


Is Winston-Salem or Kennebunkport Better for its Old Town?

Winston-Salem
Kennebunkport

Winston-Salem is a popular place for its historic old town. However, Kennebunkport does not have a historic old town.

Winston-Salem is a good destination for visiting its old town. Nearby Old Salem is filled with historic museums, gardens, and restaurants. A ticket is required for most of the venues, but the atmosphere and architecture are charming.

Kennebunkport does not have a historic old town.

Is Winston-Salem or Kennebunkport Better for Hiking?

Winston-Salem
Kennebunkport

Kennebunkport is a popular place for the nearby hiking options. However, Winston-Salem is not a hiking destination.

Kennebunkport is a good destination for hiking. There are waterfront walks and coastal trails. There are also trails that wander through forests or past marshland.

Winston-Salem is not a hiking destination.

Is the Shopping Better in Winston-Salem or Kennebunkport?

Winston-Salem
Kennebunkport

Kennebunkport is notable for its shopping areas. Also, Winston-Salem is not as famous, but is still a good city to visit for shopping.

Browsing through shops is a popular activity in Kennebunkport. Head to Dock's Square for the best local shops with a charming atmosphere.

Plenty of visitors enjoy shopping while in Winston-Salem. You'll find a mix of larger shopping malls, retail outlets, and shopping centers around town.


Is Winston-Salem or Kennebunkport Better for Families?

Winston-Salem
Kennebunkport

Kennebunkport is notable for its family-friendly activities. Also, Winston-Salem is not as famous, but is still a good city to visit for its kid-friendly activities.

Kennebunkport is known to be a very family-friendly place to visit. You can explore the rocks around Mother's Beach or take the kids out on a lobster boat. There's also a lot of history around Dock's Square and plenty of kid-friendly restaurants in town.

Winston-Salem is a family-friendly city. There are interactive museums like the Kaleideum science museums. There are also outdoor parks and playgrounds, kid-friendly restaurants, and a children's theater.

Is Winston-Salem or Kennebunkport Better for Couples?

Winston-Salem
Kennebunkport

Kennebunkport is notable for couples. However, Winston-Salem is a mediocre city for romance.

Kennebunkport is a very popular place to visit for couples. Beaches, romantic hotels, and charming local restaurants make this a perfect couple's destination.

Winston-Salem is not the best destination for a couple to visit. There are restaurants and movie theaters that make for a nice date night. There are also parks and walks that will get you outdoors.

Is Winston-Salem or Kennebunkport Better for Students?

Winston-Salem
Kennebunkport

Winston-Salem is a popular place for its student-friendly activities. However, Kennebunkport is not popular with students.

It's common for students to visit Winston-Salem. Wake Forest University as well as colleges such as Salem College give parts of the city a collegiate vibe.

Kennebunkport is not popular with students.


Is Winston-Salem or Kennebunkport Better for Public Transit? Which Is Easier to Get Around Without a Car?

Winston-Salem
Kennebunkport

Both Winston-Salem and Kennebunkport offer respectable public transit options.

Public transit is generally limited in Winston-Salem. There are bus routes, but they are limited in their frequency and convenience, making a car essential for most visitors.

Public transit is mostly limited in Kennebunkport. During the summer months there's a Shoreline Trolley that connects towns.

Is Winston-Salem or Kennebunkport a more walkable city?

Winston-Salem
Kennebunkport

Kennebunkport is a popular place for its ease of walking around. However, Winston-Salem is a mediocre city for its walkability.

Kennebunkport is a somewhat walkable town. It's downtown is compact and particularly walkable.

Winston-Salem is generally not a very walkable city. The downtown area is the most pedestrian-friendly part of town, but most of the city requires a car.

For even more information, also check out Is Winston-Salem Worth Visiting? and Is Kennebunkport Worth Visiting?.

Should I spend more time in Kennebunkport or Winston-Salem?

How long in Winston-Salem or Kennebunkport?

It's fun to spend time in either Winston-Salem or Kennebunkport. Generally, people tend to spend more time in Kennebunkport due to the larger number of activities and things to do. Usually, 1-2 days is a good amount of time for Winston-Salem, and 2-4 days is enough time in Kennebunkport.

Families should spend more time in Kennebunkport than Winston-Salem. Because of the many family-friendly attractions and fun things to do for kids in Kennebunkport, it's a great place to visit with the whole family.

Couples should spend more time in Kennebunkport than Winston-Salem. You'll find plenty of romantic sights and fun activities in Kennebunkport that are perfect for a weekend getaway or a longer couple's trip.

Backpackers and budget travelers should spend more time in Kennebunkport than Winston-Salem if your budget allows for it. With a larger number of budget-friendly sights, good nightlife, and active things to do, anyone traveling on a budget would have a good time in Kennebunkport.


  • How many days in Winston-Salem or Kennebunkport? Ideal Length of Stay
    Winston-Salem 1-2 
    Kennebunkport 2-4

One day in Winston-Salem or Kennebunkport?

Many travelers enjoy the shopping and museums when visiting the under-rated destination of Winston-Salem. Your budget might influence how long you stay. If you enjoy all that's offered here, then one day is just the right amount of time to spend here.

Even though Kennebunkport is a small town, it has plenty of activities to choose from. It's also a relaxing resort destination. Your budget might influence how long you stay. Since there is so much to do in the area, one day is probably not enough for all of it.


A weekend in Winston-Salem or Kennebunkport?

It's hard to know how much time to spend in Winston-Salem. It has many unique tourist attractions and fascinating things to do. For many, it makes a great getaway for a weekend. A weekend is usually enough time to experience most activities.

It's hard to know how much time to spend in Kennebunkport. People enjoy relaxing at one of the resorts. It has many unique tourist attractions and fascinating things to do. For many, it makes a great getaway for a weekend. A weekend is usually enough time to experience most activities.

Five days in Winston-Salem or Kennebunkport?

Travelers enjoy the nightlife and food when visiting the welcoming destination of Winston-Salem. This city offers a variety of activities to choose from. Five days is usually plenty of time to spend here with extra days to spare. With this much time, visitors often visit nearby destinations or take day trips.

Kennebunkport is a small town, so it's a great destination if you're short on time. Travelers enjoy the resorts in the area as well. This town offers a variety of activities to choose from. Five days is usually plenty of time to spend here with extra days to spare. With this much time, visitors often visit nearby destinations or take day trips.

A week in Winston-Salem or Kennebunkport?

You'll find food and shopping around the city of Winston-Salem. One week is more than enough time to enjoy everything. Take some day trips to nearby places to fill the extra days. The length of your ideal trip is an individual decision.

Kennebunkport is a small town, so you can explore the area with less time. People often spend their time relaxing at one of the resorts. One week is more than enough time to enjoy everything. Take some day trips to nearby places to fill the extra days. The length of your ideal trip is an individual decision.


For some great organized tour ideas, see The Best Romantic Tours for Couples in United States of America, The Best Polar Tours & Cruises in United States of America, The Best Walking Tours in United States of America, and The Best Tours Under $1000 in United States of America.


Which place is cheaper, Kennebunkport or Winston-Salem?

These are the overall average travel costs for the two destinations.

The average daily cost (per person) in Winston-Salem is $150, while the average daily cost in Kennebunkport is $220. These costs include accommodation (assuming double occupancy, so the traveler is sharing the room), food, transportation, and entertainment. While every person is different, these costs are an average of past travelers in each destination. What follows is a categorical breakdown of travel costs for Winston-Salem and Kennebunkport in more detail.



Accommodation
  • Accommodation Hotel or hostel for one person
    Winston-Salem $91
    Kennebunkport $124
  • Accommodation Typical double-occupancy room
    Winston-Salem $182
    Kennebunkport $248
Compare Hotels in Winston-Salem and Kennebunkport

Looking for a hotel in Winston-Salem or Kennebunkport? Prices vary by location, date, season, and the level of luxury. See below for options and compare which is best for your budget and travel style.

Hotels in Winston-Salem


Hotels in Kennebunkport


Kayak helps you find the best prices for hotels, flights, and rental cars for destinations around the world. Compare prices for multiple destinations when planning your next trip.


Our Analysis
We've analyzed the average and typical hotel prices based on guest reviews, star ratings, and hotel amenities here: Winston-Salem Hotel Prices and Kennebunkport Hotel Prices.

Local Transportation
  • Local Transportation Taxis, local buses, subway, etc.
    Winston-Salem $23
    Kennebunkport $49

Is it cheaper to fly into Winston-Salem or Kennebunkport?

Prices for flights to both Kennebunkport and Winston-Salem change regularly based on dates and travel demand. We suggest you find the best prices for your next trip on Kayak, because you can compare the cost of flights across multiple airlines for your prefered dates.





Food
  • Food Meals for one day
    Winston-Salem $42
    Kennebunkport $67

Entertainment
  • Entertainment Entrance tickets, shows, etc.
    Winston-Salem $20
    Kennebunkport $21

Tours and Activities in Winston-Salem

Some specific costs of activities, tours, and entrance tickets for Winston-Salem are as follows:

  • Carolina History & Haunts Winston-Salem Historical Ghost Tour: $26
  • Unique Scavenger Hunt Experience in Winston-Salem by Wacky Walks: $10

Tours and Activities in Kennebunkport

Also, here are some specific examples of entertainment, tickets, and activities for Kennebunkport.

  • Haunted Ghost Walking Tour: $27
  • Ghost Tour with Folklore, Gossip & Scandals: $29
  • 90 Minutes Ghost Walking Tour in Kennebunkport: $30
  • Historic District Walking Tour: $45
  • 2-Hour Historical Walking Tour: $50
  • A Tasty Lunchtime Walking Tour: $140

Alcohol
  • Alcohol Drinks for one day
    Winston-Salem $24
    Kennebunkport $31


When we compare the travel costs of actual travelers between Winston-Salem and Kennebunkport, we can see that Kennebunkport is more expensive. And not only is Winston-Salem much less expensive, but it is actually a significantly cheaper destination. So, traveling to Winston-Salem would let you spend less money overall. Or, you could decide to spend more money in Winston-Salem and be able to afford a more luxurious travel style by staying in nicer hotels, eating at more expensive restaurants, taking tours, and experiencing more activities. The same level of travel in Kennebunkport would naturally cost you much more money, so you would probably want to keep your budget a little tighter in Kennebunkport than you might in Winston-Salem.

If you're trying to decide if either of these two destinations are within your price range, also see Is Winston-Salem Expensive? and Is Kennebunkport Expensive?.


Which is Bigger, Winston-Salem or Kennebunkport?

Winston-Salem has a larger population, and is about 120 times larger than the population of Kennebunkport. When comparing the sizes of Winston-Salem and Kennebunkport, keep in mind that a larger population does not always imply the destination has more attractions or better activities. So, always research the type of place that you want to visit along with the activities and attractions that interest you.


When is the best time to visit Winston-Salem or Kennebunkport?

Both places have a temperate climate with four distinct seasons. As both cities are in the northern hemisphere, summer is in July and winter is in January.

Should I visit Winston-Salem or Kennebunkport in the Summer?

The summer brings many poeple to Winston-Salem as well as Kennebunkport. The summer months attract visitors to Winston-Salem because of the family-friendly experiences. Additionally, the hiking, the small town charm, and the family-friendly experiences are the main draw to Kennebunkport this time of year.

In the summer, Winston-Salem is a little warmer than Kennebunkport. Typically, the summer temperatures in Winston-Salem in July average around 81°F (27°C), and Kennebunkport averages at about 69°F (20°C).

The sun comes out a lot this time of the year in Kennebunkport. People are often attracted to the plentiful sunshine in Winston-Salem this time of the year. In the summer, Winston-Salem often gets around the same amount of sunshine as Kennebunkport. Winston-Salem gets 273 hours of sunny skies this time of year, while Kennebunkport receives 282 hours of full sun.

Winston-Salem receives a lot of rain in the summer. Winston-Salem usually gets more rain in July than Kennebunkport. Winston-Salem gets 4.4 inches (112 mm) of rain, while Kennebunkport receives 2.6 inches (66 mm) of rain this time of the year.


  • Summer Average Temperatures July
    Winston-Salem 81°F (27°C) 
    Kennebunkport 69°F (20°C)

Should I visit Winston-Salem or Kennebunkport in the Autumn?

Both Kennebunkport and Winston-Salem are popular destinations to visit in the autumn with plenty of activities. The shopping scene are the main draw to Winston-Salem this time of year. Also, many travelers come to Kennebunkport for the hiking trails, the shopping scene, the small town atmosphere, and the natural beauty of the area.

In October, Winston-Salem is generally much warmer than Kennebunkport. Daily temperatures in Winston-Salem average around 62°F (17°C), and Kennebunkport fluctuates around 49°F (9°C).

The sun comes out a lot this time of the year in Winston-Salem. Winston-Salem usually receives more sunshine than Kennebunkport during autumn. Winston-Salem gets 212 hours of sunny skies, while Kennebunkport receives 196 hours of full sun in the autumn.

In October, Winston-Salem usually receives less rain than Kennebunkport. Winston-Salem gets 3 inches (75 mm) of rain, while Kennebunkport receives 3.3 inches (84 mm) of rain each month for the autumn.


  • Autumn Average Temperatures October
    Winston-Salem 62°F (17°C) 
    Kennebunkport 49°F (9°C)

Should I visit Winston-Salem or Kennebunkport in the Winter?

Both Kennebunkport and Winston-Salem during the winter are popular places to visit. Many travelers come to Winston-Salem for the museums, the shopping scene, and the cuisine. Also, many visitors come to Kennebunkport in the winter for the museums, the shopping scene, and the cuisine.

Kennebunkport can get quite cold in the winter. Be prepared for some very cold days in Winston-Salem. Winston-Salem is much warmer than Kennebunkport in the winter. The daily temperature in Winston-Salem averages around 40°F (4°C) in January, and Kennebunkport fluctuates around 21°F (-6°C).

In the winter, Winston-Salem often gets around the same amount of sunshine as Kennebunkport. Winston-Salem gets 169 hours of sunny skies this time of year, while Kennebunkport receives 163 hours of full sun.

Winston-Salem usually gets around the same amount of rain in January as Kennebunkport. Winston-Salem gets 3.2 inches (82 mm) of rain, while Kennebunkport receives 3.4 inches (86 mm) of rain this time of the year.


  • Winter Average Temperatures January
    Winston-Salem 40°F (4°C) 
    Kennebunkport 21°F (-6°C)

Should I visit Winston-Salem or Kennebunkport in the Spring?

The spring attracts plenty of travelers to both Winston-Salem and Kennebunkport. Also, most visitors come to Kennebunkport for the small town charm and the natural beauty during these months.

In the spring, Winston-Salem is much warmer than Kennebunkport. Typically, the spring temperatures in Winston-Salem in April average around 61°F (16°C), and Kennebunkport averages at about 43°F (6°C).

People are often attracted to the plentiful sunshine in Kennebunkport this time of the year. In Winston-Salem, it's very sunny this time of the year. Winston-Salem usually receives more sunshine than Kennebunkport during spring. Winston-Salem gets 248 hours of sunny skies, while Kennebunkport receives 212 hours of full sun in the spring.

In April, Winston-Salem usually receives around the same amount of rain as Kennebunkport. Winston-Salem gets 3.1 inches (80 mm) of rain, while Kennebunkport receives 3.3 inches (85 mm) of rain each month for the spring.


  • Spring Average Temperatures April
    Winston-Salem 61°F (16°C) 
    Kennebunkport 43°F (6°C)

Typical Weather for Kennebunkport and Winston-Salem

Winston-Salem Kennebunkport
Temp (°C) Rain (mm) Temp (°C) Rain (mm)
Jan 40°F (4°C) 3.2 inches (82 mm) 21°F (-6°C) 3.4 inches (86 mm)
Feb 43°F (6°C) 3.4 inches (86 mm) 24°F (-5°C) 3.5 inches (89 mm)
Mar 52°F (11°C) 3.7 inches (94 mm) 33°F (1°C) 3.6 inches (91 mm)
Apr 61°F (16°C) 3.1 inches (80 mm) 43°F (6°C) 3.3 inches (85 mm)
May 69°F (21°C) 3 inches (77 mm) 53°F (12°C) 3.3 inches (85 mm)
Jun 77°F (25°C) 3.9 inches (99 mm) 63°F (17°C) 3.1 inches (79 mm)
Jul 81°F (27°C) 4.4 inches (112 mm) 69°F (20°C) 2.6 inches (66 mm)
Aug 80°F (26°C) 4.3 inches (109 mm) 67°F (20°C) 2.6 inches (66 mm)
Sep 73°F (23°C) 3.5 inches (90 mm) 59°F (15°C) 3.1 inches (78 mm)
Oct 62°F (17°C) 3 inches (75 mm) 49°F (9°C) 3.3 inches (84 mm)
Nov 53°F (12°C) 2.6 inches (67 mm) 39°F (4°C) 4.8 inches (123 mm)
Dec 44°F (7°C) 3.1 inches (80 mm) 27°F (-3°C) 4.1 inches (103 mm)