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14 Towns Like Kennebunkport, Maine

Wooden Houses at Kennebunkport, Maine.

Kennebunkport is a city in the state of Maine. The small American town is famous for its history, quaint shops and cafes, and beautiful scenery. Kennebunkport has a population of only 5,776, but that number increases as the weather warms. The seaside hamlet is a popular summer destination.

Residents and tourists alike love the coastal city in Maine for its natural beauty, slow-paced lifestyle, and general atmosphere. Kennebunkport is the perfect place to relax and enjoy the simple things in life. It offers pristine beaches, lovely gardens, and excellent seafood. It’s also home to many art galleries, museums, and antique shops. While the picturesque seascape is expensive to visit and live there, tourists and residents love Kennebunkport, ME.

If you’re looking for a Kennebunkport-like destination, many other small towns in the U.S. offer a similar experience. These 12 towns offer the same charm and character as Kennebunkport, from New England fishing villages to historic west coast cities.

1. Friday Harbor, Washington

San Juan Islands harbor at Washington.

The small town in Washington state has a population of about 2,500 people. Along with size, it has an old-fashioned charm comparable to Kennebunkport. The city is on San Juan Island and is only accessible by Washington State ferry.

Visitors come to Friday Harbor to enjoy the peace and quiet of the small island community. Most people get around the seaside town by walking, biking, and scooters. Shuttles and transportation are available for persons with disabilities.

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Friday Harbor is a great place to enjoy the outdoors. There are plenty of parks and beaches to explore. Visitors can also go whale watching, kayaking, and fishing. There are also shops and restaurants in the town.

Friday Harbor’s primary industry is tourism, but the town also has a robust agricultural sector. The San Juan Islands are an excellent stop for fresh fruits and vegetables. Like Kennebunkport, Friday Harbor is an expensive place to visit. However, the town’s natural beauty and slow-paced lifestyle make it worth the cost.

2. Westport, Connecticut

Historical building at Westport, Connecticut.

Westport is a town in Connecticut with a population of about 27,000 people. The township is on Long Island Sound, and visitors and townees flock to the area for its beaches, golf courses, and country clubs. Westport is also home to many artists, writers, and musicians.

While the seaside city is much larger than Kennebunkport, ME, the feel of the two places is comparable. Westport has a small-town vibe with big-city amenities. The town has excellent schools, a lively downtown area, and a strong sense of community.

The town’s long history and abundance of cultural attractions make it a popular destination for tourists. There are many colonial-era homes and buildings in Westport. It also has many art galleries, museums, and theaters to keep everyone busy and entertained. Visitors can also enjoy the town’s parks, beaches, and restaurants.

The charming beachside town’s primary income comes from tourism and retail. However, many residents also work in the financial sector near New York City. Westport is an affluent community, but the cost of living is high, and tourists can feel a slight pinch, too. However, the town’s charm, history, and beautiful setting make it worth the cost.

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3. Clearwater, Florida

Beautiful sunset at Clearwater, Florida.

Clearwater is a city in Florida with a population of about 107,000 people. The town is on the Gulf of Mexico and is loved by many near and far for its clear waters and white sandy beaches. The coastal city has a lot to offer tourists and residents alike.

There are many shops, restaurants, and attractions downtown. Visitors can also enjoy the town’s parks, beaches, and marinas. Clearwater is also home to several professional sports teams and Minor League Baseball’s Clearwater Threshers.

Clearwater is a welcoming community with a strong sense of pride. While the city is much larger than Kennebunkport, it has a similar charm. The people are friendly, and the town has a laid-back atmosphere. The city’s primary industry is tourism, but it’s also close to a thriving economy in Tampa.

The cost of living in Clearwater is high, but the residents agree the sunset over the Gulf is worth the price, and tourists, paying a fraction of the price for a glimpse of the same sunset (or sunrise., would have to agree.

4. Rehoboth Beach, Delaware

Historical lighthouse at Rehoboth Beach, Delaware.

Rehoboth Beach is a city in Delaware, with a population of about 1,500 people. The town is on the Atlantic Ocean and is a popular destination for beach-goers, as it has some of the best beaches in the country.

Besides its beautiful beaches, Rehoboth Beach also has a lively boardwalk and many shops and restaurants. Visitors can also enjoy the town’s parks and nature trails. Rehoboth Beach is a welcoming community with a strong sense of pride. Popular tourist stops include the Tanger Outlets, Funland, and the boardwalk.

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The people are friendly, and the town has a laid-back atmosphere, much like Kennebunkport, ME. Tourism is the #1 industry in Rehoboth Beach, but many residents that live here year round are retired or commute to nearby cities for work.

The cost of living in Rehoboth Beach is high, but the residents enjoy a relaxed lifestyle, and tourists come for the same tranquility they can’t get anywhere else, making the price well worth it.

5. Newport, Rhode Island

The Breakers mansion Newport, Rhode Island.

Newport is a city in Rhode Island with about 24,000 people. The town is on Aquidneck Island and is a popular destination for beach lovers, as it has many beaches. Newport also has several historic buildings and mansions, such as The Breakers and Marble House.

Newport has the atmosphere you need for a relaxing vacation, with a touch of history and luxury. The town is also home to the Naval War College, Salve Regina University, and many shops and restaurants. Besides its beautiful beaches and historic buildings, Newport also has a lively downtown area and many shops and restaurants. Visitors can also enjoy the town’s parks, marinas, and golf courses.

Newport is a great place to retire or raise a family for year-round residents. The town is also home to many businesses, such as Newport Shipyard, which builds and repairs luxury yachts. Yes, the beautiful shorelines mean the cost of living is a little higher in Newport, but the views are priceless and well worth the price.

6. Saint Michaels, Maryland

Navy Point Historic houses Saint Michaels, Maryland.

Another East Coast town, Saint Michaels, is in Maryland on the Eastern Shore. This seaside town of about 1,000 people is a popular destination for boaters and nature lovers. The village is on the Miles River and has many marinas and boatyards.

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Saint Michaels is also home to several historic buildings, such as the Chesapeake Bay Maritime Museum and many shops and restaurants. Popular parks include Talbot County Community Park and the St. Michaels Nature Trail. Top industries in Saint Michaels include tourism, fishing, and boatbuilding. Residents also commute to nearby cities, such as Annapolis, for work.

The town has a friendly atmosphere that’s reminiscent of Kennebunkport. The cost of living in Saint Michaels is high, but the residents enjoy the quiet, small-town lifestyle off the beaten path.

7. Chatham, Massachusetts

Atwood House Museum Chatham, Massachusetts.

For more seasonal living, Chatham is a town in Massachusetts that experiences the joy of four seasons, like Kennebunkport. This town of about 6,000 people is on Cape Cod and is a popular destination for beach lovers as it has This Cape Cod town swells in the summer as tourists come to enjoy the town’s beaches, shops, and restaurants.

Chatham is also home to several historic buildings, such as the Atwood House Museum and many parks. Famous beaches include Lighthouse Beach and Hardings Beach. The town’s economy is driven by tourism, with many businesses catering to visitors.

The town has a relaxed atmosphere that’s perfect for a summer vacation. The cost of living in Chatham is high, but the residents and tourists love the view of the ocean and the small-town feel.

8. Port Aransas, Texas

Wild life viewing Port Aransas, Texas.

Small town living isn’t limited to the East Coast, as Port Aransas, TX proves. This town of about 4,200 people is on Mustang Island and is a popular destination for beach lovers, as it has miles of sandy beaches. Port Aransas is also a famous fishing destination, as it’s known for its redfish and trout.

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Whether you’re looking to spend a few days or move to the area, Port Aransas is a great place to enjoy the sun and the sea, far away from the hustle and bustle of the city. The town is home to several shops, restaurants, and the Port Aransas Museum. Famous beaches include Port Aransas Beach and Mustang Island State Park.

Yes, it’s not cheap to live in Port Aransas, but the town’s a dream for those who love the outdoors and want to live in a small, close-knit community equivalent to Kennebunkport of Texas.

9. Rye, New Hampshire

Houses near the beach at Rye, New Hampshire.

What do you know about the coastal towns of New Hampshire? You’re on the right track if you’re thinking of Portsmouth, but there’s another excellent option—Rye. This town of about 5,000 people is on the coast of New Hampshire and is a popular destination for beach lovers, as it has seven miles of sandy beaches. Rye is also known for its fishing, with many charter boats available for hire.

The town’s economy is driven by tourism, with many businesses catering to visitors. Popular beaches include Wallis Sands State Beach and Jenness State Beach. The city is home to several shops, restaurants, and the Rye Harbour State Park.

Rye has a relaxed atmosphere that’s perfect for a summer vacation. The cost of living in Rye is high, but it’s hard to pass on the town’s ideal location and friendly community that offers vibes of Kennebunkport. As a bonus, Rye’s close to the Maine city—hope on 95 and drive north for 35 miles.

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10. Cannon Beach, Oregon

Beach coast Cannon Beach, Oregon.

Back on the West Coast, Cannon Beach is a small town in Oregon about a 3.5-hour drive from Portland with less than 1,900 residents. Many people visit Cannon Beach for its 4-mile stretch of sandy beaches, perfect for swimming, sunbathing, and surfing. If you prefer a boat on the water, charter boats are available for hire.

The town’s economy is driven by tourism, with many businesses catering to visitors. The city is home to shops, restaurants, and the Cannon Beach History Center & Museum. Other popular spots include Ecola State Park and Haystack Rock.

Cannon Beach has a relaxed atmosphere that’s perfect for a summer vacation. The cost of living in Cannon Beach is high, but the town’s proximity to Portland makes it a desirable place to live for those who want to experience the best of both worlds—the city and the beach.

11. San Clemente, California

Beach town at San Clemente, California.

You can’t have a list without at least one California town, and San Clemente fits the bill. This town of about 65,000 people is on the coast of Orange County and is a popular destination for beach lovers, as it has six miles of sandy beaches. San Clemente is also known for its surfing, with many surf schools and shops available.

It’s more than fun in the sun, though—San Clemente is also home to the San Clemente Pier, shops, restaurants, and the Surfing Heritage and Culture Center. The town’s relaxed atmosphere and small-town feel make it a great place to live for those who want to escape the hustle and bustle of Los Angeles.

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San Clemente, CA, is expensive, but it’s worth it for the town’s ideal location and friendly community. Look no further than San Clemente if you’re looking for a Kennebunkport on the West Coast.

12. Chincoteague, Virginia

Chincoteague National Wildlife Refuge.

Look no further than Chincoteague, VA, for an authentic taste of American history. This town of about 3,000 people is on Virginia’s Eastern Shore and is known for its miles of sandy beaches, fishing, crabbing, and oystering. The city is also home to the Chincoteague National Wildlife Refuge, a 14,000-acre refuge perfect for hiking, bird watching, and fishing.

The most significant industry in town is tourism, so many businesses feed off of visitors. The city is home to several shops, restaurants, and the Chincoteague Island Arts Organization. Other popular spots include Assateague Island National Seashore and the Chincoteague Pony Swim.

Chincoteague has a relaxed atmosphere, perfect for a summer vacation and ideal for year-round living. The cost of living in Chincoteague is moderate, and tourists flock to the town for its small-town charm and proximity to nature. If you’re looking for a Kennebunkport a little further south, Chincoteague is the perfect place for you.

13. Tybee Island, Georgia

Historical lighthouse Tybee Island, Georgia.

Tybee Island is a town in Georgia about 20 minutes from Savannah. This barrier island is a popular destination for miles of sandy beaches, fishing, crabbing, and kayaking and is home to almost 3,000 year-round residents. The island is also home to the Tybee Island Light Station and Museum, Fort Pulaski National Monument, and the Tybee Island Marine Science Center.

The town’s economy is driven by tourism, so you’ll find plenty of shops, restaurants, and hotels. Many come for events, such as the Tybee Island Pirate Fest and the Tybee Island Music Fest. Other famous spots include the Tybee Island Pier and Pavilion and the Tybee Island Wildlife Refuge.

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Tybee Island has a relaxed, small-town atmosphere that’s a slice of paradise for those who want to escape city life. Consider Tybee Island a lower-cost alternative to Kennebunkport, ME, for your next vacation destination or a new place to live.

14. Orange Beach, Alabama

Beautiful white sand beach at Alabama.

Look no further than Orange Beach, AL, if you’re looking for a Kennebunkport on the Gulf Coast. This town of about 6,000 people is on a barrier island and is known for its white-sand beaches, fishing, and sailing. The city is also home to the Orange Beach Indian and Sea Museum, the Hugh S. Branyon Backcountry Trail, and the Perdido Key State Park.

You’ll find plenty of shops, restaurants, and hotels in Orange Beach, as tourism is the town’s primary industry. The city hosts several events throughout the year, such as the Orange Beach Mardi Gras Parade and the Orange Beach Seafood Festival. Other popular destinations include the Orange Beach Sportsplex and the Orange Beach Arts Center.

Orange Beach is a great place to live or visit if you’re looking for a Kennebunkport-like town with a laid-back atmosphere and plenty of things to do. The cost of living is moderate, making it ideal for families or retirees.